(S)-3-(Boc-amino)-2-piperidone

Base Information

• Chemical Name: (S)-3-(Boc-amino)-2-piperidone
• CAS No.: 92235-39-7
• Molecular Formula: C10H18N2O3
• Molecular Weight: 214.265
• Hs Code.: 2933790090
• European Community (EC) Number: 821-035-5
• DSSTox Substance ID: DTXSID10238933
• Wikidata: Q72448403
• Mol file: 92235-39-7.mol

Synonyms:3-t-butyloxycarbonyl-amino-2-piperidone;3-tert-butyloxycarbonylamino-2-piperidone;t-Boc-amino-2-piperidone

Chemical Property of (S)-3-(Boc-amino)-2-piperidone

Chemical Property:

• Vapor Pressure: 8.68E-07mmHg at 25°C
• Melting Point: 203-205 °C
• Refractive Index: 1.489
• Boiling Point: 405.6 °C at 760 mmHg
• PKA: 11.05±0.20(Predicted)
• Flash Point: 199.1 °C
• PSA: 67.43000
• Density: 1.11 g/cm³
• LogP: 1.50940
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.13174244
• Heavy Atom Count: 15
• Complexity: 258

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-BocL-OrinithineLactam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCCNC1=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1CCCNC1=O
• Uses: N-Boc L-Orinithine Lactam is used in the synthesis of Pro-Leu-Gly-NH2 analogs for dopamine receptor modulation.

Technology Process of (S)-3-(Boc-amino)-2-piperidone

There total 2 articles about (S)-3-(Boc-amino)-2-piperidone 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:

Nα-(1,1-dimethylethoxycarbonyl)-Nδ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester (53054-02-7) → tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate (1394857-67-0) + 3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine (92235-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; water; hydrogenchloride; 5% Pd/C / ethanol / 24 h

2: N-ethyl-N,N-diisopropylamine / tert-butyl alcohol / 18 h / 120 °C / Inert atmosphere

With hydrogenchloride; 5% Pd/C; water; hydrogen; N-ethyl-N,N-diisopropylamine; In ethanol; tert-butyl alcohol;

DOI:10.1021/ol3021226

Reference yield:

Boc-Orn(Z)-OH (2480-93-5) → tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate (1394857-67-0) + 3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine (92235-39-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tert-butyl alcohol; dichloromethane / 24 h / 50 °C / Inert atmosphere

2: hydrogen; water; hydrogenchloride; 5% Pd/C / ethanol / 24 h

3: N-ethyl-N,N-diisopropylamine / tert-butyl alcohol / 18 h / 120 °C / Inert atmosphere

With hydrogenchloride; 5% Pd/C; water; hydrogen; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ol3021226

Reference yield: 85.0%

3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine (92235-39-7) + Benzyl bromoacetate (5437-45-6) → (3S)-benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-yl)acetate (175133-83-2,1256385-95-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm960572n

upstream raw materials:

Boc-Orn(Z)-OH

N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester

Downstream raw materials:

(3S)-3-aminopiperidin-2-one hydrochloride

(3S)-benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-yl)acetate

3(S)-[(tert-butyloxycarbonyl)amino]-2-oxo-1-piperidineacetic acid

((S)-2-Oxo-3-phenylacetylamino-piperidin-1-yl)-acetic acid

Refernces