ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate

Base Information

• Chemical Name: ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate
• CAS No.: 388108-70-1
• Molecular Formula: C₂₁H₃₂N₂O₄
• Molecular Weight: 376.496
• Mol file: 388108-70-1.mol

Synonyms:ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate

Chemical Property of ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate

There total 5 articles about ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate 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: 47.0%

→ ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate (388108-70-1)

Guidance literature:

Reference yield:

5-[(1R)-1-phenyl-ethylamino]-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (388108-67-6) → ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate (388108-70-1) + ethyl 1-(tert-butoxycarbonyl)-3-{[1-phenylethyl]amino}piperidine-4-carboxylate (1016259-54-3)

Guidance literature:

5-[(1R)-1-phenyl-ethylamino]-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester; With cobalt(II) chloride hexahydrate; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; optical yield given as %de; Inert atmosphere; Cooling with ice;

DOI:10.1055/s-0030-1259963

Reference yield:

ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride (52763-21-0) → ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate (388108-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 4 h / Autoclave

2.1: toluene / Reflux

3.1: cobalt(II) chloride hexahydrate; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] / dichloromethane; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere; Cooling with ice

With cobalt(II) chloride hexahydrate; palladium 10% on activated carbon; hydrogen; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-0030-1259963

upstream raw materials:

5-[(1R)-1-phenyl-ethylamino]-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

di-tert-butyl dicarbonate

ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride

ethyl 1-tert-butoxycarbonyl-3-oxopiperidine-4-carboxylate

Downstream raw materials:

(3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine

(3R,4R)-4-(acetylthiomethyl)-1-(tert-butoxycarbonyl)-3-{methyl[(1R)-1-phenylethyl]amino}piperidine

(3R,4R)-4-methyl-3-(methyl-((R)-1-phenylethyl)amino)piperidine-1-carboxylic acid tert-butyl ester

(3R,4R)-3-methylamino-4-methylpiperidine-1-carboxylic acid tert-butyl ester