(S)-N-Boc-piperidine-3-carboxylate methyl ester

Base Information

• Chemical Name: (S)-N-Boc-piperidine-3-carboxylate methyl ester
• CAS No.: 88466-76-6
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.29900
• Mol file: 88466-76-6.mol

Synonyms:

Chemical Property of (S)-N-Boc-piperidine-3-carboxylate methyl ester

Chemical Property:

• Boiling Point: 307.4±35.0 °C(Predicted)
• PKA: -2.48±0.40(Predicted)
• PSA: 55.84000
• Density: 1.094±0.06 g/cm3(Predicted)
• LogP: 1.74440

Purity/Quality:

99%, ^*data from raw suppliers

Methyl (S)-1-Boc-piperidine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-N-Boc-piperidine-3-carboxylate methyl ester

There total 7 articles about (S)-N-Boc-piperidine-3-carboxylate methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (88495-54-9) + methyl iodide (74-88-4) → 1-(tert-butoxycarbonyl)piperidine-(3S)-carboxylic acid methyl ester (88466-76-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

Reference yield:

3,5-Pyridinedicarboxylic acid (499-81-0) → 1-(tert-butoxycarbonyl)piperidine-(3S)-carboxylic acid methyl ester (88466-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HCl (g) / methanol

2.1: H₂ / Pd/C / acetic acid / 38000 Torr

2.2: Et₃N / CH₂Cl₂

3.1: pig liver esterase; aq. KH₂PO₄; CH₃CN / aq. H₃PO₄ / 12 h / 25 °C / pH 8.0

3.2: (S)-(-)-1-phenylethylamine / ethanol / 70 °C

4.1: ClCO₂Et; N-methylpyrrolidinone / CH₂Cl₂

4.2: Et₃N / tetrahydrofuran

5.1: t-BuSH / benzene / Irradiation

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium dihydrogenphosphate; pig liver esterase; hydrogen; chloroformic acid ethyl ester; 2-methylpropan-2-thiol; acetonitrile; palladium on activated charcoal; In methanol; dichloromethane; phosphoric acid; acetic acid; benzene;

DOI:10.1016/S0040-4039(03)00002-9

Reference yield:

dimethyl pyridine-3,5-dicarboxylate hydrochloride → 1-(tert-butoxycarbonyl)piperidine-(3S)-carboxylic acid methyl ester (88466-76-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / Pd/C / acetic acid / 38000 Torr

1.2: Et₃N / CH₂Cl₂

2.1: pig liver esterase; aq. KH₂PO₄; CH₃CN / aq. H₃PO₄ / 12 h / 25 °C / pH 8.0

2.2: (S)-(-)-1-phenylethylamine / ethanol / 70 °C

3.1: ClCO₂Et; N-methylpyrrolidinone / CH₂Cl₂

3.2: Et₃N / tetrahydrofuran

4.1: t-BuSH / benzene / Irradiation

With 1-methyl-pyrrolidin-2-one; potassium dihydrogenphosphate; pig liver esterase; hydrogen; chloroformic acid ethyl ester; 2-methylpropan-2-thiol; acetonitrile; palladium on activated charcoal; In dichloromethane; phosphoric acid; acetic acid; benzene;

DOI:10.1016/S0040-4039(03)00002-9

upstream raw materials:

3,5-Pyridinedicarboxylic acid

1-tert-butyl 3,5-dimethyl piperidine-1,3,5-tricarboxylate

(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

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

Downstream raw materials:

(S)-methyl piperidine-3-carboxylate

tert-butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate

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