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

Base Information

• Chemical Name: (3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine
• CAS No.: 1312762-41-6
• Molecular Formula: C₂₀H₃₂N₂O₃
• Molecular Weight: 348.486
• Mol file: 1312762-41-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine 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: 93.0%

ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{methyl[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate → (3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-41-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling with ice;

DOI:10.1055/s-0030-1259963

Reference yield:

ethyl (3R,4R)-1-(tert-butoxycarbonyl)-3-{[(1R)-1-phenylethyl]amino}piperidine-4-carboxylate (388108-70-1) → (3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 1.5 h / 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere; Cooling with ice

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice

With lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-0030-1259963

Reference yield:

ethyl 1-tert-butoxycarbonyl-3-oxopiperidine-4-carboxylate (71233-25-5) → (3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-41-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene / Reflux

2.1: 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

2.2: 20 °C / Inert atmosphere; Cooling with ice

3.1: dichloromethane / 1.5 h / 20 °C / Inert atmosphere

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

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling with ice

With lithium aluminium tetrahydride; cobalt(II) chloride hexahydrate; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; In tetrahydrofuran; 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

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

di-tert-butyl dicarbonate

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

Downstream raw materials:

(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

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