Boc-3-Hydroxy-1-adamantyl-D-glycine supplier

: N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In ethanol at 18 - 65℃; for 2h;	98.1%

: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 24424-99-5
di-tert-butyl dicarbonate

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;	98%
With potassium phosphate In tetrahydrofuran; sodium hydroxide at 20℃; for 2h;	88%
Stage #1: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate With sodium hydroxide for 4h; pH=10; Stage #2: With sulfuric acid In Isopropyl acetate; water for 0.0833333 - 0.166667h; pH=2.0 - 8;	88%

: N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With (1R,2S)-2-Amino-1,2-diphenylethanol In ethyl acetate at 20℃; for 2h; Reflux; Resolution of racemate;	56%
Multi-step reaction with 2 steps 1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate 2: hydrogenchloride / ethyl acetate; water / pH 3 View Scheme
Multi-step reaction with 2 steps 1: ethanol / 0.08 h / Resolution of racemate; Reflux 2: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme

: 361441-97-6
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

A: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

B: 681282-72-4
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions

Conditions	Yield
With potassium hydroxide; potassium permanganate at 60 - 90℃; for 1.5h;	A 51% B 17%
With potassium hydroxide; potassium permanganate In water at 60 - 90℃; for 1.5h;	A 51% B 17%

: 361441-97-6
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With potassium permanganate; water; potassium hydroxide at 60 - 90℃; for 1.5h;	51%
With potassium permanganate; potassium hydroxide at 90℃;	49%
With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 25℃;	18.6 g

: 361441-95-4
(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 2: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 3: 4.07 g / K2CO3 / dimethylformamide / 19 h 4: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride; water / acetic acid / 80 °C 2: hydrogen; palladium 10% on activated carbon / acetic acid 3: triethylamine / methanol 4: potassium permanganate; potassium hydroxide / 90 °C View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 2.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 3.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 3.2: 0 - 5 °C 4.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride; water / acetic acid / 18 h / 80 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 3: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 4: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme

: (R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 2: 4.07 g / K2CO3 / dimethylformamide / 19 h 3: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen; palladium 10% on activated carbon / acetic acid 2: triethylamine / methanol 3: potassium permanganate; potassium hydroxide / 90 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 2.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 2.2: 0 - 5 °C 3.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 2: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 3: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme

: 770-71-8
1-adamantanemethanol

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 2: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 3: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 4: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 5: 4.07 g / K2CO3 / dimethylformamide / 19 h 6: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 6 steps 1.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C 1.2: 0 - 5 °C 2.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 3.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 4.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 5.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 5.2: 0 - 5 °C 6.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme
Multi-step reaction with 6 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux 3.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C 4.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 5.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 6.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 7 steps 1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium bromide / dichloromethane; water / 12 h / 5 - 30 °C 2.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C 3.1: sulfuric acid / 45 - 50 °C 3.2: 2 h / 20 - 35 °C 4.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr 5.1: sulfuric acid / 110 - 112 °C 6.1: sulfuric acid; nitric acid / 10 - 25 °C 7.1: sodium hydroxide / 5 h / 25 - 30 °C View Scheme

: 828-51-3
1-Adamantanecarboxylic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C 2: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 3: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 4: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 5: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 6: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 7: 4.07 g / K2CO3 / dimethylformamide / 19 h 8: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 8 steps 1.1: thionyl chloride / 3 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C 3.2: 0 - 5 °C 4.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 5.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 6.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 7.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 7.2: 0 - 5 °C 8.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme
Multi-step reaction with 8 steps 1.1: thionyl chloride / 4 h / Reflux 2.1: sodium / Petroleum ether / 20 °C 2.2: 20 °C 2.3: 6 h / Reflux 3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C 4.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 5.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 6.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 7.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C 8.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme

: 2094-74-8
1-Adamantanecarbaldehyde

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 2: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 3: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 4: 4.07 g / K2CO3 / dimethylformamide / 19 h 5: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 5 steps 1: sodium hydrogensulfite / 0 - 60 °C 2: hydrogenchloride; water / acetic acid / 80 °C 3: hydrogen; palladium 10% on activated carbon / acetic acid 4: triethylamine / methanol 5: potassium permanganate; potassium hydroxide / 90 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 2.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 3.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 4.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 4.2: 0 - 5 °C 5.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme
Multi-step reaction with 5 steps 1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux 2: hydrogenchloride; water / acetic acid / 18 h / 80 °C 3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 4: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 5: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C 2.1: sulfuric acid / 45 - 50 °C 2.2: 2 h / 20 - 35 °C 3.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr 4.1: sulfuric acid / 110 - 112 °C 5.1: sulfuric acid; nitric acid / 10 - 25 °C 6.1: sodium hydroxide / 5 h / 25 - 30 °C View Scheme

: 711-01-3
methyl adamantane-1-carboxylate

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 3: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 4: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 5: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 6: 4.07 g / K2CO3 / dimethylformamide / 19 h 7: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C 2.2: 0 - 5 °C 3.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 4.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 5.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 6.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 6.2: 0 - 5 °C 7.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 3.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux 4.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C 5.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 6.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 7.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme

: 95853-35-3
(S)-(+)-β-amino-1-adamantaneacetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.07 g / K2CO3 / dimethylformamide / 19 h 2: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 10 - 25 °C 2: sodium hydroxide / 5 h / 25 - 30 °C View Scheme

: (αS)-α-[(1,1-dimethylethoxy)carbonyl]amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate pH=3;

: 1334321-39-9
N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; isobutyl chloroformate / tetrahydrofuran / 1.5 h / -8 °C 1.2: 18 h / -8 - 25 °C 2.1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate 3.1: hydrogenchloride / ethyl acetate; water / pH 3 View Scheme
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 5 h / 20 °C 1.2: 53 h / 20 - 50 °C 1.3: 2 h 2.1: ethanol / 0.08 h / Resolution of racemate; Reflux 3.1: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme

: 102502-64-7
(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / methanol 2: potassium permanganate; potassium hydroxide / 90 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 2: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme

: 59768-71-7, 60256-21-5, 95853-35-3, 100926-41-8
2-(adamantan-1-yl)-2-aminoacetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 2: potassium permanganate; potassium hydroxide / 2 h / 90 °C 3: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme

: 1660-04-4
1-acetyladamantane

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C 2: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 3: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 4: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 5: potassium permanganate; potassium hydroxide / 2 h / 90 °C 6: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme

Yield

Multi-step reaction with 6 steps
1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
2: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
3: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
4: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
5: potassium permanganate; potassium hydroxide / 2 h / 90 °C
6: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme

: 16091-98-8
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 2: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 3: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 4: potassium permanganate; potassium hydroxide / 2 h / 90 °C 5: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme

: 16091-97-7
1-adamantyl-2-hydroxyiminoacetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 2: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 3: potassium permanganate; potassium hydroxide / 2 h / 90 °C 4: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme

: 2094-72-6
1-Adamantanecarbonyl chloride

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium / Petroleum ether / 20 °C 1.2: 20 °C 1.3: 6 h / Reflux 2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C 3.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 4.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 5.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 6.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C 7.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium / Petroleum ether / 20 °C
1.2: 20 °C
1.3: 6 h / Reflux
2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
3.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
4.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
5.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
6.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C
7.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme

: 3-hydroxytricyclo[3.3.1.13'7]decane-1-carbaldehyde

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 2.1: water / 0.17 h / 0 - 2 °C 2.2: 14.5 h / -4 - 80 °C 3.1: hydrogenchloride; water / 1 h / 24 - 80 °C 3.2: 12 h / 80 - 82 °C 4.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 5.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 5.2: 2.08 h / 3 - 26 °C 5.3: 12 h / 40 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
2.1: water / 0.17 h / 0 - 2 °C
2.2: 14.5 h / -4 - 80 °C
3.1: hydrogenchloride; water / 1 h / 24 - 80 °C
3.2: 12 h / 80 - 82 °C
4.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
5.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
5.2: 2.08 h / 3 - 26 °C
5.3: 12 h / 40 °C
View Scheme

: C11H17O5S(1-)*Na(1+)

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: water / 0.17 h / 0 - 2 °C 1.2: 14.5 h / -4 - 80 °C 2.1: hydrogenchloride; water / 1 h / 24 - 80 °C 2.2: 12 h / 80 - 82 °C 3.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 4.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 4.2: 2.08 h / 3 - 26 °C 4.3: 12 h / 40 °C View Scheme

: (2S)-[((1S)-2-hydroxy-1-phenylethyl)amino]-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)ethanenitrile

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water / 1 h / 24 - 80 °C 1.2: 12 h / 80 - 82 °C 2.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 3.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 3.2: 2.08 h / 3 - 26 °C 3.3: 12 h / 40 °C View Scheme

: (2S)-[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]-[((1S)-2-hydroxy-1-phenylethyl)amino]ethanoic acid hydrochloride

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 2.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 2.2: 2.08 h / 3 - 26 °C 2.3: 12 h / 40 °C View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: (2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Stage #1: (2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride With water; potassium carbonate In tetrahydrofuran at 3 - 10℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 3 - 26℃; for 2.08333h; Stage #3: With water at 40℃; for 12h;	1.16 g

: 42711-75-1
3-hydroxyadamantane-1-carboxylic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 31 °C 1.2: 14.5 h / 0 - 30 °C 1.3: 1 h / 0 - 10 °C 2.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C 3.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 4.1: water / 0.17 h / 0 - 2 °C 4.2: 14.5 h / -4 - 80 °C 5.1: hydrogenchloride; water / 1 h / 24 - 80 °C 5.2: 12 h / 80 - 82 °C 6.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 7.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 7.2: 2.08 h / 3 - 26 °C 7.3: 12 h / 40 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 31 °C
1.2: 14.5 h / 0 - 30 °C
1.3: 1 h / 0 - 10 °C
2.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C
3.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
4.1: water / 0.17 h / 0 - 2 °C
4.2: 14.5 h / -4 - 80 °C
5.1: hydrogenchloride; water / 1 h / 24 - 80 °C
5.2: 12 h / 80 - 82 °C
6.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
7.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
7.2: 2.08 h / 3 - 26 °C
7.3: 12 h / 40 °C
View Scheme

: 38584-37-1
1-hydroxy-3-hydroxymethyladamantane

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C 2.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 3.1: water / 0.17 h / 0 - 2 °C 3.2: 14.5 h / -4 - 80 °C 4.1: hydrogenchloride; water / 1 h / 24 - 80 °C 4.2: 12 h / 80 - 82 °C 5.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 6.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 6.2: 2.08 h / 3 - 26 °C 6.3: 12 h / 40 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C
2.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C
3.1: water / 0.17 h / 0 - 2 °C
3.2: 14.5 h / -4 - 80 °C
4.1: hydrogenchloride; water / 1 h / 24 - 80 °C
4.2: 12 h / 80 - 82 °C
5.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr
6.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C
6.2: 2.08 h / 3 - 26 °C
6.3: 12 h / 40 °C
View Scheme

: 143467-20-3
1-acetyl-3-chloroadamantane

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: potassium hydroxide / water / 6 h / Reflux 2: potassium hydroxide; potassium permanganate / water; tert-butyl alcohol / 4.5 h / 35 - 45 °C 3: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h / 0 - 5 °C / pH 7 4: sodium hydroxide; nickel-aluminum alloy / water / 50 °C 5: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10 6: ethanol / 0.08 h / Resolution of racemate; Reflux 7: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme

Yield

Multi-step reaction with 7 steps
1: potassium hydroxide / water / 6 h / Reflux
2: potassium hydroxide; potassium permanganate / water; tert-butyl alcohol / 4.5 h / 35 - 45 °C
3: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h / 0 - 5 °C / pH 7
4: sodium hydroxide; nickel-aluminum alloy / water / 50 °C
5: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10
6: ethanol / 0.08 h / Resolution of racemate; Reflux
7: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme

: C12H18NO3(1-)*Na(1+)

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10 2: ethanol / 0.08 h / Resolution of racemate; Reflux 3: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme

: C17H27NO5*C20H24N2O2

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate pH=2;	0.96 g

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 709031-45-8
(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid

: 361442-01-5
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile Solvent; Large scale;	98.1%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;	46%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 841302-41-8
cis-2-azabicyclo[3.1.0]hexane hydrochloride

: 841302-42-9
(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;	97.5%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 59483-84-0
bis(pentafluorophenyl)carbonate

: pentafluorophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions

Conditions	Yield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h; Stage #2: bis(pentafluorophenyl)carbonate In ethyl acetate at 25℃; for 2h;	93.1%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 1312338-82-1
D-cis-4,5-methanoprolineamide methanesulfonic acid salt

: 1564266-87-0
(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;	93%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 1659-31-0
2,2'-dipyridyl carbonate

: 2-pyridyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions

Conditions	Yield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h; Stage #2: 2,2'-dipyridyl carbonate In ethyl acetate at 25℃; for 3h;	92.2%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 865999-64-0
(1S)-α-amino-3-hydroxyadamantane-acetic acid hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; isopropyl alcohol at 10 - 35℃; for 8h;	90%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 5070-13-3
bis-(p-nitrophenyl) carbonate

: 4-nitrophenyl (2S)-2-((t-butoxycarbonyl)amino)-2-(3-hydroxyadamantan-1-yl)acetate

Conditions

Conditions	Yield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 0.666667h; Stage #2: bis-(p-nitrophenyl) carbonate In N,N-dimethyl-formamide at 70℃; for 5h; Solvent;	90%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: (S)-N-boc-(3-hydroxyadamantan-1-yl)glycine succinimide ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 1h;	90%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide

: 361442-01-5
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions

Conditions	Yield
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.5h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃; for 4.5h;	89.3%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: (2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

: 361442-01-5
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions

Conditions	Yield
With TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;	85%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 280-57-9
1,4-diaza-bicyclo[2.2.2]octane

: 709031-42-5
(<αS)-<α[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.137] decane-1-acetic acid DABCO salt

Conditions

Conditions	Yield
In Isopropyl acetate; water; ethyl acetate at 20℃;	79%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 1564266-70-1
L-trans-4,5-methanoprolineamide methanesulfonic acid salt

: (S)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;	79%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 1564266-74-5
D-trans-4,5-methanoprolineamide methanesulfonic acid salt

: 1564267-02-2
(S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h;	71%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 841302-37-2
(1RS,5SR)-2-azabicyclo[3.1.0]hexane hydrochloride

A: 841302-55-4
(2R,3S)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

B: 841302-42-9
(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;	A 27.4% B 40.6%

...Expand

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 681282-72-4
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions

Conditions	Yield
With potassium permanganate; potassium hydroxide In water at 60 - 85℃; for 1.5h;	25%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 24426-40-2
N-(cyanomethyl)ethylamine

: [(cyanomethyl-ethyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 5616-32-0
(methylamino)acetonitrile

: [(cyanomethyl-methyl-carbamoyl)-(3-hydroxy-adamantan-1-yl)-methyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 2-amino-N-cyanomethyl-2-(3-hydroxy-adamantan-1-yl)-N-methyl-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: EDAC; HOAt; Et3N / CH2Cl2 2: TFA / CH2Cl2 View Scheme

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 2-amino-N-cyanomethyl-N-ethyl-2-(3-hydroxy-adamantan-1-yl)-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: EDAC; HOAt; Et3N / CH2Cl2 2: TFA / CH2Cl2 View Scheme

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: [(S)-2-((1S,3S,5S)-3-Cyano-2-aza-bicyclo[3.1.0]hex-2-yl)-1-(3-fluoro-adamantan-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C 3: 82 percent / imidazole; pyridine; POCl3 / -20 °C View Scheme
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere 3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere View Scheme

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 709031-43-6
3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 2.2: 20 - 25 °C / pH > 10 View Scheme
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 18 h / 20 °C View Scheme

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 361442-06-0
(S)-N-Boc-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere View Scheme

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: (S)-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C 3: 72 percent / CH2Cl2 / 0.5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere 3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C View Scheme

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

: 361442-05-9
(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C 3.1: 95 percent / CH2Cl2 / 2.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C 1.2: 15.5 h / -7 - 10 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C 2.2: 7 - 15 °C / pH 10 - 10.5 3.1: dichloromethane / -5 - 2 °C View Scheme
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere 3: 1H-imidazole; pyridine; trichlorophosphate / 0.75 h / -30 °C / Inert atmosphere 4: water / dichloromethane / 1.5 h / 0 °C View Scheme

Product Name

Boc-3-Hydroxy-1-adamantyl-D-glycine

Synthetic route

Boc-3-Hydroxy-1-adamantyl-D-glycine Specification

Related Products

Hot Products