Product Name

  • Name

    Ethyl (3S)-piperidine-3-carboxylate

  • EINECS 609-464-4
  • CAS No. 37675-18-6
  • Article Data16
  • CAS DataBase
  • Density 1.003 g/cm3
  • Solubility
  • Melting Point
  • Formula C8H15NO2
  • Boiling Point 238.6 °C at 760 mmHg
  • Molecular Weight 157.213
  • Flash Point 90.6 °C
  • Transport Information
  • Appearance liquid
  • Safety 26-36/37/39-39-36
  • Risk Codes 36/37/38-41
  • Molecular Structure Molecular Structure of 37675-18-6 (Ethyl (3S)-piperidine-3-carboxylate)
  • Hazard Symbols IrritantXi
  • Synonyms 3-Piperidinecarboxylicacid, ethyl ester, (S)-;(+)-Ethyl nipecotate;(S)-(+)-Ethyl nipecotate;(S)-Ethyl nipecotate;Ethyl(S)-3-piperidinecarboxylate;Ethyl (S)-nipecotate;3-Piperidinecarboxylicacid, ethyl ester, (3S)-;
  • PSA 38.33000
  • LogP 0.87790

Synthetic route

(S)-ethyl nipecotate (S,S)-hydrogen tartrate

(S)-ethyl nipecotate (S,S)-hydrogen tartrate

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃;89%
With sodium hydroxide In water at 0℃;89%
In water at 0℃; pH=13; Decomposition;65%
With sodium hydroxide In water
C4H6O6*C8H15NO2
183316-65-6

C4H6O6*C8H15NO2

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In water89%
Ethyl nipecotate
71962-74-8

Ethyl nipecotate

A

(R)-ethyl nipecotate
25137-01-3

(R)-ethyl nipecotate

B

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Stage #1: Ethyl nipecotate With L-Tartaric acid
Stage #2: With potassium carbonate
A 20%
B n/a
With L-Tartaric acid In ethanol; acetone at 20℃; resolution;
With L-Tartaric acid In ethanol Resolution of racemate; optical yield given as %ee;
With L-Tartaric acid Resolution of racemate;
Ethyl nipecotate
71962-74-8

Ethyl nipecotate

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
With D-tartaric acid
Resolution of racemate;
(3S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester
174699-11-7

(3S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal In ethanol for 3h;
(4R)-3-({(3S)-1-[(benzyloxy)carbonyl]piperidin-3-yl}carbonyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one
868632-22-8

(4R)-3-({(3S)-1-[(benzyloxy)carbonyl]piperidin-3-yl}carbonyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C
2: rac. camphersulfonic acid / 15 h / Heating
3: H2; AcOH / Pd/C / ethanol / 3 h
View Scheme
5-bromovaleroyl chloride
4509-90-4

5-bromovaleroyl chloride

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: BuLi / tetrahydrofuran / 0.17 h / -30 °C
1.2: 87 percent / tetrahydrofuran / 2 h / 0 °C
2.1: TiCl4; Et3N / CH2Cl2 / 0.5 h / -15 °C
2.2: TiCl4 / CH2Cl2 / 3 h / 0 °C
3.1: 80 percent / NaH; Bu4NI / dimethylformamide / 3 h / 70 °C
4.1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C
5.1: rac. camphersulfonic acid / 15 h / Heating
6.1: H2; AcOH / Pd/C / ethanol / 3 h
View Scheme
(3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid
88466-74-4

(3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: rac. camphersulfonic acid / 15 h / Heating
2: H2; AcOH / Pd/C / ethanol / 3 h
View Scheme
(4R)-3-(5-bromo-1-oxopentyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one
637337-43-0

(4R)-3-(5-bromo-1-oxopentyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: TiCl4; Et3N / CH2Cl2 / 0.5 h / -15 °C
1.2: TiCl4 / CH2Cl2 / 3 h / 0 °C
2.1: 80 percent / NaH; Bu4NI / dimethylformamide / 3 h / 70 °C
3.1: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C
4.1: rac. camphersulfonic acid / 15 h / Heating
5.1: H2; AcOH / Pd/C / ethanol / 3 h
View Scheme
(4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-5-bromo-1-oxopentyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one
637337-59-8

(4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-5-bromo-1-oxopentyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / NaH; Bu4NI / dimethylformamide / 3 h / 70 °C
2: 85 percent / H2O2; LiOH*H2O / tetrahydrofuran; H2O / 4 h / 0 °C
3: rac. camphersulfonic acid / 15 h / Heating
4: H2; AcOH / Pd/C / ethanol / 3 h
View Scheme
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel; dioxane / 165 °C / 110326 - 220652 Torr / Hydrogenation
2: Dg-tartaric acid
View Scheme
salt of (D)-2-(4-hydroxyphenoxy)propionic acid with ethyl 3-piperidinecarboxylate

salt of (D)-2-(4-hydroxyphenoxy)propionic acid with ethyl 3-piperidinecarboxylate

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
With sodium carbonate In diethyl ether at 20℃; for 2h;1.15 g
ethanol
64-17-5

ethanol

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride at 100℃; for 6h; Inert atmosphere;
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl N-carbethoxy-piperidine-3S-carboxylate
1346514-04-2

ethyl N-carbethoxy-piperidine-3S-carboxylate

Conditions
ConditionsYield
With 4-methyl-morpholine In chloroform at 0 - 20℃;100%
(R)-2-fluoro-4-(1-hydroxybutyl)benzoic acid

(R)-2-fluoro-4-(1-hydroxybutyl)benzoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-1-(2-fluoro-4-((1R)-1-hydroxybutyl)benzoyl)piperidine-3-carboxylic acid ethyl ester

(S)-1-(2-fluoro-4-((1R)-1-hydroxybutyl)benzoyl)piperidine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;99%
acetic anhydride
108-24-7

acetic anhydride

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-nipecotic acid ethyl ester

(S)-nipecotic acid ethyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;99%
(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Conditions
ConditionsYield
Stage #1: (S)-(+)-nipecotic acid ethyl ester With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 0.333333h; Heating / reflux;
Stage #2: With sodium sulfate In tetrahydrofuran; diethyl ether; water
98%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2.33333h; Heating / reflux;98%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2.33333h; Heating / reflux;98%
Stage #1: (S)-(+)-nipecotic acid ethyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h;
Stage #2: With potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 15h;
With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran at 50 - 66℃; for 4.5h; Inert atmosphere;
isopentanoyl chloride
108-12-3

isopentanoyl chloride

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-ethyl 1-(3-methylbutanoyl)piperidine-3-carboxylate
1554631-89-8

(S)-ethyl 1-(3-methylbutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;97.5%
9-methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxylic acid
1121526-82-6

9-methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxylic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(3S)-ethyl 1-(9-methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonyl)piperidine-3-carboxylate
1121527-59-0

(3S)-ethyl 1-(9-methyl-3-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h;97%
2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride
952674-99-6

2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)piperidine-3-carboxylate

ethyl (3S)-1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,1-dichloroethane at 80℃; for 1h;96%
With N-ethyl-N,N-diisopropylamine In 1,1-dichloroethane at 80℃; for 1h;96%
(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-2-(benzyloxycarbonylaminomethyl)-3-phenylpropanoic acid
261174-46-3

(S)-2-(benzyloxycarbonylaminomethyl)-3-phenylpropanoic acid

Cbz-(S)β2hPhe-(S)β2hPro-OEt
764704-88-3

Cbz-(S)β2hPhe-(S)β2hPro-OEt

Conditions
ConditionsYield
With 4-methyl-morpholine; HATU In dichloromethane at 0 - 25℃;95%
(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-piperidine-3-carboxylic acid ethyl ester hydrochloride

(S)-piperidine-3-carboxylic acid ethyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; toluene at 60℃; Cooling;95%
Multi-step reaction with 3 steps
1: 74 percent / CH2Cl2 / 16 h / 20 °C
2: 90 percent / LiOH / methanol; H2O / 72 h / 20 °C
3: HCl / 1.5 h / 110 °C
View Scheme
formic acid
64-18-6

formic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

C9H17NO2

C9H17NO2

Conditions
ConditionsYield
In methanol at 0℃; for 6h; Reflux;93.4%
4-[(4-chloro-2-(2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid
922161-60-2

4-[(4-chloro-2-(2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-(4-[(4-chloro-2-(2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
922161-61-3

ethyl (3S)-1-(4-[(4-chloro-2-(2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h;92%
N-(3,5-dichlorophenyl)picolinamide
879824-11-0

N-(3,5-dichlorophenyl)picolinamide

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

C20H21Cl2N3O3

C20H21Cl2N3O3

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; copper(II) acetate monohydrate; magnesium chloride In 1,4-dioxane at 20℃; for 4h; Inert atmosphere;92%
3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propionic acid
937054-53-0

3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propionic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-piperidinecarboxylate
937055-14-6

ethyl (3S)-1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-piperidinecarboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;91%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 14.6h;
4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)-methyl]-6-(3-hydroxypropoxy)phenyl)(2,2-dimethylpropyl)-amino]-4-oxobutanoic acid
922161-64-6

4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)-methyl]-6-(3-hydroxypropoxy)phenyl)(2,2-dimethylpropyl)-amino]-4-oxobutanoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxypropoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
1334531-23-5

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxypropoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h;88%
2,6-Dichloropyrimidine
3934-20-1

2,6-Dichloropyrimidine

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-ethyl 1-(2-chloropyrimidin-4-yl)piperidine-3-carboxylate
1347758-03-5

(S)-ethyl 1-(2-chloropyrimidin-4-yl)piperidine-3-carboxylate

Conditions
ConditionsYield
With triethylamine In ethanol at 0 - 23℃; for 18h; Inert atmosphere;88%
formic acid
64-18-6

formic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-formylpiperidine-3-carboxylate

ethyl (3S)-1-formylpiperidine-3-carboxylate

Conditions
ConditionsYield
In toluene for 4.5h; Reflux; Dean-Stark;88%
formaldehyd
50-00-0

formaldehyd

ethanol
64-17-5

ethanol

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl 1-(ethoxymethyl)piperidine-3-carboxylate

ethyl 1-(ethoxymethyl)piperidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: ethanol; (S)-(+)-nipecotic acid ethyl ester With potassium carbonate at 0℃; for 0.25h; Inert atmosphere;
Stage #2: formaldehyd at 25℃; for 6h; Inert atmosphere;
88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (S)-1-[(tert-butoxy)carbonyl]piperidine-3-carboxylate
191599-51-6

ethyl (S)-1-[(tert-butoxy)carbonyl]piperidine-3-carboxylate

Conditions
ConditionsYield
In dichloromethane87%
With triethylamine In dichloromethane at 20℃; for 3h;87%
With triethylamine In dichloromethane at 20℃; for 3h;87%
(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid
88495-54-9

(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

Boc-(S)-β2-HPro-(S)-β2-HPro-OEt
253790-54-4

Boc-(S)-β2-HPro-(S)-β2-HPro-OEt

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In chloroform at 0℃; for 16h; Acylation; peptide coupling;87%
4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid
922161-76-0

4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-(4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
922161-77-1

ethyl (3S)-1-(4-[(4-chloro-2-(3-hydroxy-2,2-dimethylpropoxy)-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h;87%
3-chloro-2-methylbenzoic acid
7499-08-3

3-chloro-2-methylbenzoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-ethyl 1-(3-chloro-2-methylbenzoyl)piperidine-3-carboxylate
1430424-36-4

(S)-ethyl 1-(3-chloro-2-methylbenzoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;86%
(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

tert-butyl 2-(3-bromophenoxy)-2-methylpropanoate
393186-07-7

tert-butyl 2-(3-bromophenoxy)-2-methylpropanoate

ethyl (S)-1-(3-((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)phenyl)piperidine-3-carboxylate

ethyl (S)-1-(3-((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)phenyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos In toluene at 80℃;82%
4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)-methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid
922161-82-8

4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)-methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
922161-83-9

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(3-hydroxy-3-methylbutoxy)phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h;81%
2-bromo-4-fluoro-pyridine
357927-50-5

2-bromo-4-fluoro-pyridine

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

(S)-ethyl 1-(2-bromopyridin-4-yl)piperidine-3-carboxylate

(S)-ethyl 1-(2-bromopyridin-4-yl)piperidine-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 100℃;81%
With potassium carbonate In dimethyl sulfoxide at 100℃;81%
(S)-(+)-2-(4-cyanophenyl)oxirane
179694-33-8

(S)-(+)-2-(4-cyanophenyl)oxirane

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-[(2S)-2-(4-cyanophenyl)-2-hydroxyethyl]piperidine-3-carboxylate
1265323-48-5

ethyl (3S)-1-[(2S)-2-(4-cyanophenyl)-2-hydroxyethyl]piperidine-3-carboxylate

Conditions
ConditionsYield
With dmap In isopropyl alcohol at 50℃; Inert atmosphere; stereospecific reaction;80%
Stage #1: (S)-(+)-2-(4-cyanophenyl)oxirane; (S)-(+)-nipecotic acid ethyl ester In isopropyl alcohol at 55℃; for 4h; Inert atmosphere;
Stage #2: With dmap In isopropyl alcohol at 50℃; for 12h;
72%
4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl 4-methylbenzenesulfonate
148319-31-7

4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl 4-methylbenzenesulfonate

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate
148319-28-2

ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone for 44h; Ambient temperature;79%
4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methoxyphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid
922160-87-0

4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methoxyphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methoxyphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
922160-92-7

ethyl (3S)-1-(4-[(4-chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-methoxyphenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h;74%
4-[(4-chloro-2-ethoxy-6-[(S)-hydroxy(2-methoxyphenyl)-methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid
922161-43-1

4-[(4-chloro-2-ethoxy-6-[(S)-hydroxy(2-methoxyphenyl)-methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoic acid

(S)-(+)-nipecotic acid ethyl ester
37675-18-6

(S)-(+)-nipecotic acid ethyl ester

A

ethyl (3S)-1-(4-[(4-chloro-2-ethoxy-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
922161-44-2

ethyl (3S)-1-(4-[(4-chloro-2-ethoxy-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

B

ethyl (3S)-1-(4-[(4-chloro-2-ethoxy-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate
922161-44-2

ethyl (3S)-1-(4-[(4-chloro-2-ethoxy-6-[(S)-hydroxy(2-methoxyphenyl)methyl]phenyl)(2,2-dimethylpropyl)amino]-4-oxobutanoyl)piperidine-3-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h;A 7%
B 74%

Ethyl (3S)-piperidine-3-carboxylate Chemical Properties

Molecular Structure of Ethyl (3S)-piperidine-3-carboxylate (CAS NO.37675-18-6):

IUPAC Name: Ethyl (3S)-piperidine-3-carboxylate
Canonical SMILES: CCOC(=O)C1CCCNC1
Isomeric SMILES: CCOC(=O)[C@H]1CCCNC1
InChI: InChI=1S/C8H15NO2/c1-2-11-8(10)7-4-3-5-9-6-7/h7,9H,2-6H2,1H3/t7-/m0/s1
InChIKey: XIWBSOUNZWSFKU-ZETCQYMHSA-N
Molecular Weight: 157.2102 [g/mol]
Molecular Formula: C8H15NO2
XLogP3: 0.1
H-Bond Donor: 1
H-Bond Acceptor: 3 
Index of Refraction: 1.448
Molar Refractivity: 41.99 cm3
Molar Volume: 156.6 cm3
Surface Tension: 32 dyne/cm
Density: 1.003 g/cm3
Flash Point: 90.6 °C
Enthalpy of Vaporization: 47.55 kJ/mol
Boiling Point: 238.6 °C at 760 mmHg
Vapour Pressure: 0.042 mmHg at 25 °C
storage temp.: Refrigerator
Product Categories: Nitrogen cyclic compounds; Piperidine; Heterocyclic Compounds; Chiral Building Blocks; Esters (Chiral); Synthetic Organic Chemistry

Ethyl (3S)-piperidine-3-carboxylate Safety Profile

Safety Information of Ethyl (3S)-piperidine-3-carboxylate (CAS NO.37675-18-6):
Hazard Codes: IrritantXi
Risk Statements: 36/37/38-41 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R41:Risk of serious damage to the eyes.
Safety Statements: 26-36/37/39-39-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S39:Wear eye / face protection. 
S36:Wear suitable protective clothing.

Ethyl (3S)-piperidine-3-carboxylate Specification

 Ethyl (3S)-piperidine-3-carboxylate (CAS NO.37675-18-6), its Synonyms are 3-Piperidinecarboxylicacid, ethyl ester, (S)- ; (+)-Ethyl nipecotate ; (S)-(+)-Ethyl nipecotate ; (S)-Ethyl nipecotate ; Ethyl(S)-3-piperidinecarboxylate .

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