N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester

Base Information

• Chemical Name: N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester
• CAS No.: 254905-66-3
• Molecular Formula: C₂₃H₃₇N₃O₃
• Molecular Weight: 403.565
• Mol file: 254905-66-3.mol

Synonyms:N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester

Chemical Property of N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester

There total 5 articles about N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl 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)-3-(dimethylaminomethyl)piperidine-1-carboxylic acid tert-butyl ester (254905-64-1,1002359-82-1) → dihydrochloride salt of N,N-dimethyl-N-(((3R)piperidin-3-yl)methyl)amine (1211495-34-9) + N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (254905-66-3)

Guidance literature:

With hydrogenchloride; In ethyl acetate;

Reference yield:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine (37553-65-4,64263-83-8,85466-66-6) + N,N-dimethyl-N-(((3R)-piperidin-3-yl)methyl)amine dihydrochloride (1211495-34-9) → N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (254905-66-3)

Guidance literature:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

N,N-dimethyl-N-(((3R)-piperidin-3-yl)methyl)amine dihydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 72h;

DOI:10.1016/S0223-5234(02)01370-3

Reference yield:

(3R)-3-formylpiperidine-1-carboxylic acid tert-butyl ester (194726-46-0) → N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (254905-66-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 866 mg / NaB(OAc)3H; AcOH; molecular sieves / CH₂Cl₂; ethanol / 16 h / 20 °C

2.1: HCl / ethyl acetate / 0.75 h / 20 °C

3.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

3.2: 1.69 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; molecular sieve; sodium tris(acetoxy)borohydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0223-5234(02)01370-3

upstream raw materials:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine

N,N-dimethyl-N-(((3R)-piperidin-3-yl)methyl)amine dihydrochloride

(3S)-3-(dimethylaminomethyl)piperidine-1-carboxylic acid tert-butyl ester

(3R)-3-formylpiperidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2R)-1-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-methylamino-3-phenylpropan-1-one

(1-{(2E)-3-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]allyl}cyclobutyl)carbamic acid tert-butyl ester

{(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester

N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamic acid tert-butyl ester