N-Boc-pyrroline supplier | CasNO.73286-70-1

Name
N-Boc-pyrroline
EINECS
CAS No. 73286-70-1
Article Data81
CAS DataBase
Density 1.056 g/cm³
Solubility Slightly soluble in water.
Melting Point 40.0 to 44.0 °C
Formula C₉H₁₅NO₂
Boiling Point 219.889 °C at 760 mmHg
Molecular Weight 169.224
Flash Point 86.786 °C
Transport Information
Appearance White to yellow low melting solid or liquid
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-(tert-Butoxycarbonyl)-3-pyrroline;1-t-Butoxycarbonyl-3-pyrroline;1-tert-Butoxycarbonylpyrroline;1-tert-Butyloxycarbonyl-3-pyrroline;2,5-Dihydro-1H-pyrrole-1-carboxylic acid1,1-dimethylethyl ester;2,5-Dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester;2,5-Dihydropyrrole-1-carboxylic acid tert-butyl ester;N-Boc-2,5-dihydropyrrole;tert-Butyl3-pyrroline-1-carboxylate;
PSA 29.54000
LogP 1.73120

Synthetic route

: 109-96-6
3-Pyrroline

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

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
In tetrahydrofuran; water at 0 - 20℃; for 3.16667h;	100%
In dichloromethane at 0 - 20℃; Inert atmosphere;	100%
In dichloromethane at 0 - 20℃; for 18.58h; Inert atmosphere;	100%

: 151259-38-0
tert-butyl diallylcarbamate

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In toluene at 50℃; for 8h; Glove box;	99%
With Grubbs catalyst first generation In dichloromethane for 2h; Inert atmosphere; Reflux;	99%
[RuCl2(=CHCH3)(PCy3)2] In dichloromethane at 20℃; for 15h;	98%

: 109-96-6
3-Pyrroline

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 50℃; for 15h;	87.5%

: 109-96-6
3-Pyrroline

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

A: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

B: 86953-79-9
tert-butyl pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With pyrrolidine; sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 24h;	A 87% B n/a
In ethyl acetate at 0 - 20℃;	A 63% B 37%
In ethyl acetate at 0 - 10℃;

...Expand

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

: 63468-63-3
2,5-dihydro-1H-pyrrole hydrochloride

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With triethylamine In methanol at 0 - 20℃;	85%

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

poly(ethylene glycol)-3400 bis[p-({2-[(2,5-dihydro-1H-pyrrol-1-yl)sulfonyl]ethyl}dimethylsilyl)phenyl] ether: poly(ethylene glycol)-3400 bis[p-({2-[(2,5-dihydro-1H-pyrrol-1-yl)sulfonyl]ethyl}dimethylsilyl)phenyl] ether

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 110℃;	80%

: 1211531-07-5
tert-butyl di(but-3-en-1-yl)carbamate

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With Grubbs catalyst first generation In dichloromethane at 20℃; for 17h;	73%

: 1476-11-5
Z-1,4-dichlorobutene

: 4248-19-5
tert-butyl carbamate

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20 - 50℃; for 5.66667h;	60%
With sodium hydride In N,N-dimethyl-formamide	57%
Stage #1: tert-butyl carbazate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.25h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide; mineral oil at 80℃; for 5h;

: 215791-95-0
tert-butyl thiomorpholine-4-carboxylic acid-1,1-dioxide

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With 1,2-dibromo-1,1,2,2-tetrachloroethane; alumina-supported potassium hydroxide In tetrahydrofuran; tert-butyl alcohol at 20℃; for 4h; Ramberg-Baecklund Rearrangement;	52%

: 1476-11-5
Z-1,4-dichlorobutene

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
Stage #1: tert-butyl carbazate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 20 - 65℃; for 20.25h;	51%

: 54880-27-2
(Z)-4-chlorobut-2-en-1-amine hydrochloride

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

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With potassium carbonate	45%

: 764-41-0
1,4-dichloro-2-butene

: 4248-19-5
tert-butyl carbamate

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
Stage #1: 1,4-dichloro-2-butene With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: tert-butyl carbazate In N,N-dimethyl-formamide at 0 - 65℃;	45%

: 219668-54-9
N-Boc-N-allyl-cis-cinnamylamine

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh In methanol at 45℃; for 2h; Yield given;

: 219668-51-6
N-Allyl-N-tert-butylcarbonyl-N-cinnamylamine

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh In methanol at 45℃; for 30h; Yield given;

: 95-48-7
ortho-cresol

: 127423-61-4
tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate

A: C16H23O3N

B: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;

...Expand

: 95-48-7
ortho-cresol

: 132945-75-6
(S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate

A: 3-o-tolyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

B: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;

...Expand

: 108-39-4
3-methyl-phenol

: 127423-61-4
tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate

A: C16H23O3N

B: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;

...Expand

: 108-39-4
3-methyl-phenol

: 132945-75-6
(S)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate

A: C16H23O3N

B: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; Title compound not separated from byproducts.;

...Expand

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

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / cyclohexane 2: 98 percent / Cl2Ru(PCy3)2CHMe / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: 98 percent / NH3 / ethanol / 0 - 20 °C 2: 60 percent / NaH / dimethylformamide / 5.67 h / 20 - 50 °C View Scheme
Multi-step reaction with 2 steps 1: 93 percent / cyclohexane / 20 h / 20 °C 2: 98 percent / Cl2Ru(PCy3)2CHMe / CH2Cl2 / 15 h / 20 °C View Scheme

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

pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium: pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / CH2Cl2 / 8 h / 0 °C 2: 74 percent / NaH / dimethylformamide 3: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 2 h / 45 °C View Scheme
Multi-step reaction with 3 steps 1: 97 percent / CH2Cl2 / 8 h / 0 °C 2: 80 percent / NaH / dimethylformamide / 16 h / 60 °C 3: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 30 h / 45 °C View Scheme

: 78888-18-3
N-tert-butoxycarbonylprop-2-en-1-amine

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / NaH / dimethylformamide 2: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 2 h / 45 °C View Scheme
Multi-step reaction with 2 steps 1: 80 percent / NaH / dimethylformamide / 16 h / 60 °C 2: <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh / methanol / 30 h / 45 °C View Scheme

: 123-75-1
pyrrolidine

: 109-96-6
3-Pyrroline

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

A: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

B: 86953-79-9
tert-butyl pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
In ethyl acetate at 0 - 20℃;
In ethyl acetate at 0 - 20℃;

...Expand

: 123-75-1
pyrrolidine

: 109-96-6
3-Pyrroline

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

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
In tetrahydrofuran
In tetrahydrofuran
In tetrahydrofuran

...Expand

: 109-96-6
3-Pyrroline

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

A: 1124345-33-0
2,2',5,5'-tetrahydro-1,1'-bipyrrole

B: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
In methanol at 25℃; for 25h; Large scale reaction;	A n/a B 57.5 kg

...Expand

: 109-96-6
3-Pyrroline

: 34619-03-9
tert-butyldicarbonate

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
In methanol

: 1476-11-5
Z-1,4-dichlorobutene

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

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
With potassium carbonate In methanol Delepine reactions;

: 220655-09-4
tert-butyl thiomorpholine-4-carboxylate

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 2: 1,2-dibromo-1,1,2,2-tetrachloroethane; alumina-supported potassium hydroxide / tetrahydrofuran; tert-butyl alcohol / 4 h / 20 °C View Scheme

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 114214-49-2
1-tert-butoxycarbonyl-3,4-epoxypyrrolidine

Conditions

Conditions	Yield
With Oxone; ethylenediaminetetraacetic acid In various solvent(s)	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 12h;	100%
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With N-Bromosuccinimide In water; dimethyl sulfoxide at 0 - 25℃; for 4h; Stage #2: With sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 3h; Solvent; Temperature;	96%

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 109-96-6
3-Pyrroline

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 25℃; for 4h;	100%
With trifluoroacetic acid In dichloromethane at 25℃; for 4h;
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: (±)-trans-tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water In acetonitrile	100%
With N-Bromosuccinimide In water; dimethyl sulfoxide at 0 - 25℃; for 17h;	74%
With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 2h;

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 298681-10-4
trans tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone for 0.5h; Stage #2: N-(tert-butoxycarbonyl)-3-pyrroline In water; acetone for 20h;	100%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; tert-butyl alcohol at 20℃; for 4h;	51%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water at 20 - 25℃; for 5h;
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In acetone at 20℃; for 18h;
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 0 - 20℃; for 18h; Inert atmosphere;	4.31 g

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 86953-79-9
tert-butyl pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With tetrahydroxydiboron; palladium 10% on activated carbon; water In dichloromethane at 20℃; for 60h; Inert atmosphere;	97%
With water; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;	87%

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 107-21-1
ethylene glycol

: 1358783-14-8
3-bromo-4-(2-hydroxyethoxy)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With N-Bromosuccinimide for 18h;	97%
With N-Bromosuccinimide In 1,2-dimethoxyethane at 20℃; for 16h;	89.11%
With N-Bromosuccinimide at 20℃; for 0.333333h; Darkness;	60%
With N-Bromosuccinimide at 15℃; for 16h; Inert atmosphere;

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: rac-trans-3-bromo-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 2h;	95%

: 75-25-2
Bromoform

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: tert-butyl 6,6-dibromo-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions

Conditions	Yield
With sodium tert-pentoxide In n-heptane at -10 - 0℃; for 6h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Large scale;	95%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In ethanol; dichloromethane; water at 40 - 50℃; for 18h;	35%
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In dichloromethane; water at 0 - 20℃; for 2h; Inert atmosphere;
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In dichloromethane at 25℃; for 12h; Inert atmosphere;

: 594-20-7
2,2-dichloropropane

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: C12H21NO2

Conditions

Conditions	Yield
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction;	91%

: 5464-77-7
N,N-dibenzylformamide

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 497163-57-2
tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions

Conditions	Yield
With titanium(IV) isopropylate; methylmagnesium chloride; cyclohexylmagnesium bromide In tetrahydrofuran; diethyl ether for 0.25h; Heating;	90%
Stage #1: N-(tert-butoxycarbonyl)-3-pyrroline With titanium(IV) isopropylate; methylmagnesium chloride In tetrahydrofuran at 5 - 10℃; for 3h; Large scale; Stage #2: N,N-dibenzylformamide In tetrahydrofuran at 10 - 35℃; for 3.5h; Large scale; Stage #3: With cyclohexylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran at 30 - 40℃; for 10h; Large scale;	35%

: 69843-08-9
1-(1,1,1-trifluoroprop-2-en-2-yl)-4-methoxybenzene

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: tert-butyl 2-(3,3-difluoro-2-(4-methoxyphenyl)allyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); Triethoxysilane; lithium fluoride In dimethyl sulfoxide at 60℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	89%

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 616-38-6
carbonic acid dimethyl ester

: 202477-57-4
1-(tert-butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 0℃;	87%
With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 5℃; for 1h;	83%
With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2h;

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 698-16-8
benzohydroximoyl chloride

: 1253183-36-6
tert-butyl 3-phenyl-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazole-5(4H)-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In ethyl acetate at 90℃; for 0.166667h;	87%
With potassium carbonate In ethyl acetate at 90℃; under 5171.62 Torr; for 0.166667h; Inert atmosphere;	69%

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 114214-49-2
rac-tert-butyl (1R,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;	86%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h;	82%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 12h; Inert atmosphere;	75%

: 50-00-0
formaldehyd

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: (+/-)-1,1-dimethylethyl-2-(phenylmethyl)hexahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In ethanol; toluene at 80℃; for 24h;	85%

...Expand

: 50-00-0
formaldehyd

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 1,1-dimethylethyl-2-(phenylmethyl)hexahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

Conditions

Conditions	Yield
With triethylamine In ethanol; toluene at 80℃; for 24h;	85%

...Expand

: 20549-68-2
1-(3-iodopropoxy)benzene

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: tert-butyl 2-(3-phenoxypropyl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With potassium fluoride; nickel(II) iodide hydrate; diethoxymethylane; C16H16N2O In N,N-dimethyl acetamide at 25℃; Inert atmosphere; Sealed tube; regioselective reaction;	84%

: 74213-24-4
N-dibromomethylidenehydroxylamine

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: tert-butyl (+/-)-3-bromo-3a,4,6,6a-tetrahydro-5H-pyrrolo[3,4-d]isoxazole-5-carboxylate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate for 72h;	82%
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 72h; Cycloaddition;	80.7%

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: tert-butyl 6,6-difluoro-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions

Conditions	Yield
With sodium iodide In tetrahydrofuran at 65℃; Inert atmosphere;	81%
With sodium iodide In tetrahydrofuran for 8h; Reflux;	67%

: 29527-87-5
(2-iodopropyl)benzene

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: (±)-tert-butyl 2-(1-phenylpropan-2-yl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With potassium fluoride; nickel(II) iodide hydrate; diethoxymethylane; C16H16N2O In N,N-dimethyl acetamide at 25℃; Inert atmosphere; Sealed tube;	81%

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 1017782-17-0
tert-butyl 3-bromo-4-hydroxypyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With N-Bromosuccinimide In water; dimethyl sulfoxide at 0 - 25℃; for 4h; Inert atmosphere;	78%
With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 4.5h;
With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 20℃; for 2h;	5 g

: 5813-48-9
Methanesulfenyl chloride

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 74-89-5
methylamine

: trans-1-N-tert-butoxycarbonyl-3-methylamino-4-methylthiopyrrolidine

Conditions

Conditions	Yield
Stage #1: Methanesulfenyl chloride; N-(tert-butoxycarbonyl)-3-pyrroline In dichloromethane at 20℃; for 24h; Stage #2: methylamine In tetrahydrofuran; water at 70℃; for 15h;	77%

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: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: rac-tert-butyl (3R,4S)-3,4-dihydroxypyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 5h;	77%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 28℃; for 16h;	61.06%
With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃;	59%

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 188858-92-6
6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide

A: (1S,2S,5R,3'aR,3'bS,7'aS)-2'-t-butoxycarbonyl-2-isopropyl-5,5'-dimethyl-1H-decahydro-spiro[cyclohexane-1,6'-7'-oxa-2',5',6'a-triazacyclopenta[a]pentalen-4'-one]

B: (1S,2S,5R,3'aR,3'bS,7'aS)-1'-t-butoxycarbonyl-2-isopropyl-5,5'-dimethyl-1H-decahydro-spiro[cyclohexane-1,6'-7'-oxa-2',5',6'a-triazacyclopenta[a]pentalen-4'-one]

Conditions

Conditions	Yield
In toluene at 140℃; for 10.5h; Inert atmosphere; Sealed tube; Microwave irradiation; enantioselective reaction;	A 21% B 74%

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N-Boc-pyrroline Chemical Properties

Molecule structure of N-Boc-3-pyrroline (CAS NO.73286-70-1):

IUPAC Name: tert-Butyl 2,5-dihydropyrrole-1-carboxylate
Molecular Weight: 169.2209 g/mol
Molecular Formula: C₉H₁₅NO₂
Density: 1.055 g/cm³
Boiling Point: 219.9 °C at 760 mmHg
Flash Point: 86.8 °C
Index of Refraction: 1.491
Molar Refractivity: 46.43 cm³
Molar Volume: 160.2 cm³
Polarizability: 18.4×10^-24 cm³
Surface Tension: 37.5 dyne/cm
Enthalpy of Vaporization: 45.63 kJ/mol
Vapour Pressure: 0.116 mmHg at 25 °C
XLogP3-AA: 1.3
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Exact Mass: 169.110279
MonoIsotopic Mass: 169.110279
Topological Polar Surface Area: 29.5
Heavy Atom Count: 12
Complexity: 195
Canonical SMILES: CC(C)(C)OC(=O)N1CC=CC1
InChI: InChI=1S/C9H15NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-5H,6-7H2,1-3H3
InChIKey: YEBDZDMYLQHGGZ-UHFFFAOYSA-N
Product Categories: Pyrrolidine series; Pyrroles & Indoles; Pyrroles & Indoles

N-Boc-pyrroline Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

N-Boc-pyrroline Specification

N-Boc-3-pyrroline (CAS NO.73286-70-1) is also named as 1H-pyrrole-1-carboxylic acid, 2,5-dihydro-, 1,1-dimethylethyl ester ; 2,5-Dihydro-pyrrole-1-carboxylic acid tert-butyl ester ; 2-Methyl-2-propanyl 2,5-dihydro-1H-pyrrole-1-carboxylate ; tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate ; tert-Butyl-2,5-dihydro-1H-pyrrol-1-carboxylat ; 2,5-Dihydro-1H-pyrrole, N-BOC protected ; 3-Pyrroline, N-BOC protected . N-Boc-3-pyrroline (CAS NO.73286-70-1) is white to yellow low melting solid or liquid.

Product Name

N-Boc-pyrroline

Synthetic route

N-Boc-pyrroline Chemical Properties

N-Boc-pyrroline Safety Profile

N-Boc-pyrroline Specification

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