(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In water | 89% |
Ethyl nipecotate
A
(R)-ethyl nipecotate
B
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
With D-tartaric acid | |
Resolution of racemate; |
(3S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Raney nickel; dioxane / 165 °C / 110326 - 220652 Torr / Hydrogenation 2: Dg-tartaric acid View Scheme |
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
With sodium carbonate In diethyl ether at 20℃; for 2h; | 1.15 g |
ethanol
(S)-nipecotic acid
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
With thionyl chloride at 100℃; for 6h; Inert atmosphere; |
chloroformic acid ethyl ester
(S)-(+)-nipecotic acid ethyl ester
ethyl N-carbethoxy-piperidine-3S-carboxylate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In chloroform at 0 - 20℃; | 100% |
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h; | 99% |
acetic anhydride
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 99% |
(S)-(+)-nipecotic acid ethyl ester
(S)-(hydroxymethyl)piperidine
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
(S)-ethyl 1-(3-methylbutanoyl)piperidine-3-carboxylate
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(S)-2-(benzyloxycarbonylaminomethyl)-3-phenylpropanoic acid
Cbz-(S)β2hPhe-(S)β2hPro-OEt
Conditions | Yield |
---|---|
With 4-methyl-morpholine; HATU In dichloromethane at 0 - 25℃; | 95% |
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h; | 88% |
2,6-Dichloropyrimidine
(S)-(+)-nipecotic acid ethyl ester
(S)-ethyl 1-(2-chloropyrimidin-4-yl)piperidine-3-carboxylate
Conditions | Yield |
---|---|
With triethylamine In ethanol at 0 - 23℃; for 18h; Inert atmosphere; | 88% |
formic acid
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
In toluene for 4.5h; Reflux; Dean-Stark; | 88% |
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
ethyl (S)-1-[(tert-butoxy)carbonyl]piperidine-3-carboxylate
Conditions | Yield |
---|---|
In dichloromethane | 87% |
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
(S)-(+)-nipecotic acid ethyl ester
Boc-(S)-β2-HPro-(S)-β2-HPro-OEt
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
(S)-ethyl 1-(3-chloro-2-methylbenzoyl)piperidine-3-carboxylate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 86% |
(S)-(+)-nipecotic acid ethyl ester
tert-butyl 2-(3-bromophenoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 100℃; | 81% |
With potassium carbonate In dimethyl sulfoxide at 100℃; | 81% |
(S)-(+)-2-(4-cyanophenyl)oxirane
(S)-(+)-nipecotic acid ethyl ester
ethyl (3S)-1-[(2S)-2-(4-cyanophenyl)-2-hydroxyethyl]piperidine-3-carboxylate
Conditions | Yield |
---|---|
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
(S)-(+)-nipecotic acid ethyl ester
ethyl (S)-1-<4-(3-methyl-2-thienyl)-4-(2-thienyl)-3-butenyl>-3-piperidinecarboxylate
Conditions | Yield |
---|---|
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
(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
Conditions | Yield |
---|---|
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
(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
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
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2.5h; | A 7% B 74% |
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
Safety Information of Ethyl (3S)-piperidine-3-carboxylate (CAS NO.37675-18-6):
Hazard Codes: Xi
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 (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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