(S)-Alaninol
di-tert-butyl dicarbonate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 20℃; for 3h; | 100% |
With triethylamine In methanol at 20℃; for 12h; | 100% |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h; | 100% |
(S)-N-(tert-butoxycarbonyl)alanine methyl ester
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; methanol at 65℃; for 1h; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; | 97% |
With RuH(η1-BH4)(dppp)((R,R)-dpen); hydrogen In tetrahydrofuran at 80℃; under 37503.8 Torr; for 16h; Autoclave; | 96% |
(S)-2-aminobutan-1-ol
di-tert-butyl dicarbonate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; | 97% |
L-N-Boc-Ala
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0℃; other substrates, also with LiAlH4 and DIBAL; | 95% |
With borane-THF In tetrahydrofuran at 0℃; | 95% |
Stage #1: L-N-Boc-Ala With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine In 1,2-dimethoxyethane at 20℃; for 3h; Esterification; Stage #2: With sodium tetrahydroborate In water at 0℃; Reduction; | 90% |
N-(tert-butoxycarbonyl)-L-alanine pentachlorophenyl ester
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; iodine In tetrahydrofuran at 20℃; Reduction; | 89% |
(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 0.5h; | 89% |
D-Alanine
di-tert-butyl dicarbonate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Stage #1: D-Alanine With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Reflux; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; dichloromethane; water at 60℃; for 6h; | 63% |
(-)-tert-butyl [(1S)-1-methylprop-2-en-1-yl]carbamate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C 1.2: 20 °C 2.1: sodium tetrahydroborate / diethyl ether; methanol / 20 °C View Scheme |
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol Yield given; |
Boc-Ala-O-N-hydroxysuccinimide
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 2.5h; | |
With sodium tetrahydroborate In water at 0℃; | 0.28 g |
C12H21NO6
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water at 0℃; |
L-N-Boc-Ala
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NEt3 / tetrahydrofuran / -10 °C 2: NaBH4 / H2O / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 77 percent / EDC / CH2Cl2 / 16 h / -8 - 4 °C 2: NaBH4 / tetrahydrofuran / 2.5 h / 20 °C View Scheme |
di-tert-butyl dicarbonate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. NaOH / dioxane / 20 °C 2: NEt3 / tetrahydrofuran / -10 °C 3: NaBH4 / H2O / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 97 percent / NaHCO3; NaCl / CHCl3; H2O / 3 h / Heating 2: 91 percent / NaBH4; LiCl / tetrahydrofuran; ethanol / 16 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine / tetrahydrofuran / 20 - 50 °C 2.1: lithium aluminum hydride / tetrahydrofuran / 0.33 h 2.2: aq. potassium hydroxide / tetrahydrofuran / 1 h / 20 °C View Scheme |
Boc-Ala-H
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) zinc, AlMe3 / 1.) THF, hexane, 25 deg C, 15 min, 2.) -30 to -20 deg C, 5 h View Scheme | |
With lithium borohydride | |
With sodium tetrahydroborate | |
With sodium tetrahydroborate In methanol; diethyl ether at 20℃; | 51.8 mg |
(S)-Alaninol
tert-butyldicarbonate
1,1-dimethylethylenediamine
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
In water; tert-butyl alcohol |
Boc-Ala-O-COO-isoBu
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water Inert atmosphere; | |
With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; |
iminodicarboxylic acid di-tert-butyl ester
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine / tetrahydrofuran / 0.08 h / Inert atmosphere; Schlenk technique 1.2: 1 h / 50 °C / Inert atmosphere; Schlenk technique 2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C 3.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C 3.2: 20 °C 4.1: sodium tetrahydroborate / diethyl ether; methanol / 20 °C View Scheme |
(-)-di-tert-butyl [(1S)-1-methylprop-2-en-1-yl]imidodicarbonate
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C 2.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C 2.2: 20 °C 3.1: sodium tetrahydroborate / diethyl ether; methanol / 20 °C View Scheme |
(S)-2-t-butoxycarbonylaminopropan-1-ol
Boc-Ala-H
Conditions | Yield |
---|---|
With water; Dess-Martin periodane In dichloromethane at 20℃; for 1h; | 100% |
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.25h; Stage #2: With triethylamine In dichloromethane at -78 - 0℃; for 0.583333h; | 99% |
With Dess-Martin periodane; tert-butyl alcohol In dichloromethane Ambient temperature; | 97% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
methanesulfonyl chloride
(2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 4h; Inert atmosphere; | 100% |
With triethylamine In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate | 98.1% |
With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 98% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
tert-butyl (4S)-4-methyl-2-oxido-1,2,3-oxathiazolidin-2-ium-3-carboxylate
Conditions | Yield |
---|---|
With 1H-imidazole; thionyl chloride; triethylamine In dichloromethane at -50 - 0℃; for 4.5h; | 100% |
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With 1H-imidazole; thionyl chloride; triethylamine Stage #2: In dichloromethane at 20℃; | 100% |
With 1H-imidazole; thionyl chloride; triethylamine In dichloromethane at -60 - -55℃; for 3.5h; | 100% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
N-(Benzyloxycarbonyl)glycine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride | 100% |
With dmap In N,N-dimethyl-formamide at 20℃; | 10.45 g |
(S)-2-t-butoxycarbonylaminopropan-1-ol
tert-butyldimethylsilyl chloride
(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; | 99% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; |
(S)-2-t-butoxycarbonylaminopropan-1-ol
methanesulfonyl chloride
methanesulfonic acid 2-tert-butoxycarbonylamino-propyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 0.5h; | 98% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
5-bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione
5-bromo-1-(2,6-difluorobenzyl)-3-[2-(S)-N-Boc-aminopropyl]-6-methyluracil
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction; | 96.1% |
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran Mitsunobu reaction; | |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; | |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction; |
(S)-2-t-butoxycarbonylaminopropan-1-ol
isobutyryl chloride
Conditions | Yield |
---|---|
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol; isobutyryl chloride With dmap; triethylamine In dichloromethane at 0 - 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃; for 2h; | 96% |
phthalimide
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h; | 92% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; Inert atmosphere; | 69% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 3h; |
Chloro-oxo-acetic acid
(S)-2-t-butoxycarbonylaminopropan-1-ol
Boc-Ala-H
Conditions | Yield |
---|---|
With potassium hydrogensulfate; sodium hydrogencarbonate; triethylamine In hexane; dichloromethane; water | 92% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
acetyl chloride
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane at 20℃; for 4h; | 92% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
3-phenyl-1-(1H-pyrrol-1-yl)-1-propanone
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 18h; Sealed tube; chemoselective reaction; | 92% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
tert-butyl N-[(1S)-2-iodo-1-methylethyl]carbamate
Conditions | Yield |
---|---|
With 1H-imidazole; polystyryl diphenyl phosphine-iodine In dichloromethane for 1h; Heating; | 90% |
With 1H-imidazole; diphenylphosphinopolystyrene; iodine In dichloromethane for 1h; Heating; | 90% |
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; Cooling; | 89% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; | 90% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
(S)-2-(methylamino)propan-1-ol hydrochloride
Conditions | Yield |
---|---|
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In n-heptane at 90℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate for 0.25h; | 90% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
1-azido-(S)-2-(N-tert-butoxycarbonyl)aminopropane
Conditions | Yield |
---|---|
With sodium azide; diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70℃; | 89% |
Multi-step reaction with 2 steps 1: TEA / tetrahydrofuran / 0 °C 2: NaN3 / dimethylformamide / 55 - 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 82 percent / triethylamine / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 30 min 2: 89 percent / sodium azide / hexamethylphosphoric acid triamide / 6 h / 55 °C View Scheme |
(S)-2-t-butoxycarbonylaminopropan-1-ol
4-chlorobenzoyl chloride
4-Bromo-benzoic acid (S)-2-tert-butoxycarbonylamino-propyl ester
Conditions | Yield |
---|---|
With pyridine at 20℃; for 0.5h; | 88% |
With pyridine at 23℃; |
(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement; | 88% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
p-toluenesulfonyl chloride
(S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane
Conditions | Yield |
---|---|
With pyridine at 4℃; | 87% |
In pyridine; dichloromethane | 87% |
In pyridine; dichloromethane | 87% |
NH-pyrazole
(S)-2-t-butoxycarbonylaminopropan-1-ol
Conditions | Yield |
---|---|
Stage #1: NH-pyrazole; (S)-2-t-butoxycarbonylaminopropan-1-ol With triphenylphosphine In ethyl acetate at 10℃; for 4h; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate In ethyl acetate at 10 - 20℃; Inert atmosphere; | 86.8% |
(S)-2-t-butoxycarbonylaminopropan-1-ol
N-2-nitrobenzenesulfonamideglycine methyl ester
[(2-tert-butoxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester
Conditions | Yield |
---|---|
With dialkyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Mitsunobu reaction; | 86% |
6-bromo-pyridin-3-ol
(S)-2-t-butoxycarbonylaminopropan-1-ol
tert-butyl {(1S)-2-[(6-bromopyridin-3-yl)oxy]-1-methylethyl}carbamate
Conditions | Yield |
---|---|
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In 1,4-dioxane at 60℃; for 1h; | 86% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 20℃; for 3h; |
(S)-2-t-butoxycarbonylaminopropan-1-ol
thioacetic acid
(S)-2-<(tert-Butoxycarbonyl)amino>propyl thioacetate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate | 85% |
Stage #1: (S)-2-t-butoxycarbonylaminopropan-1-ol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 1h; Stage #2: tiolacetic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 7.5 g |
Molecular structure of N-Boc-L-alaninol (CAS NO.79069-13-9) is:
Product Name: N-Boc-L-alaninol
CAS Registry Number: 79069-13-9
IUPAC Name: tert-Butyl N-[(2S)-1-hydroxypropan-2-yl]carbamate
Molecular Formula: C8H17NO3
Molecular Weight: 175.2255
Density: 1.025 g/cm3
Melting Point: 58-61 °C
Boiling Point: 276.4 °C at 760 mmHg
Flash Point: 121 °C
Freely Rotating Bonds: 5
Index of Refraction: 1.45
Molar Refractivity: 45.94 cm3
Molar Volume: 170.8 cm3
Surface Tension: 33.9 dyne/cm
Enthalpy of Vaporization: 59.78 kJ/mol
Vapour Pressure: 0.000597 mmHg at 25°C
Product Categories: N-BOC;straight chain compounds;Amino Acids;Amino Alcohols;Boc-Amino acid series
N-Boc-L-alaninol (CAS NO.79069-13-9) is used as pharmaceutical intermediate.
Safety Statements: 22-24/25
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
WGK Germany: 3
F: 9-21
F 9: Keep under nitrogen.
F 21: Sensitive to humidity.
N-Boc-L-alaninol , its cas register number is 79069-13-9. It also can be called Boc-alaninol ; Boc-ala-ol ; Boc-L-alaninol ; Boc-L-ala-oL ; Boc-(S)-2-amino-1-propanol ; (S)-(-)-2-(tert-Butoxycarbonylamino)-1-propanoL ; (S)-2-(tert-Butoxycarbonylamino)-1-propanol ; (S)-2-(tert-Butyloxycarbonyl-amino)-1-propanol .
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