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

Base Information

• Chemical Name: (3R,4R)-4-(acetylthiomethyl)-1-(tert-butoxycarbonyl)-3-{methyl[(1R)-1-phenylethyl]amino}piperidine
• CAS No.: 1312762-42-7
• Molecular Formula: C₂₂H₃₄N₂O₃S
• Molecular Weight: 406.59
• Mol file: 1312762-42-7.mol

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

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

There total 7 articles about (3R,4R)-4-(acetylthiomethyl)-1-(tert-butoxycarbonyl)-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: 88.0%

(3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-41-6) + tiolacetic acid (507-09-5) → (3R,4R)-4-(acetylthiomethyl)-1-(tert-butoxycarbonyl)-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-42-7)

Guidance literature:

(3R,4R)-1-(tert-butoxycarbonyl)-4-hydroxymethyl-3-{methyl[(1R)-1-phenylethyl]amino}piperidine; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; Inert atmosphere; Cooling with ice; Reflux;

tiolacetic acid; In tetrahydrofuran; for 0.5h; Inert atmosphere;

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)-4-(acetylthiomethyl)-1-(tert-butoxycarbonyl)-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-42-7)

Guidance literature:

Multi-step reaction with 3 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

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / Inert atmosphere; Cooling with ice; Reflux

3.2: 0.5 h / Inert atmosphere

With lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction;

DOI:10.1055/s-0030-1259963

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3R,4R)-4-(acetylthiomethyl)-1-(tert-butoxycarbonyl)-3-{methyl[(1R)-1-phenylethyl]amino}piperidine (1312762-42-7)

Guidance literature:

Multi-step reaction with 6 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

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

4.2: 20 °C / Inert atmosphere; Cooling with ice

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

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / Inert atmosphere; Cooling with ice; Reflux

6.2: 0.5 h / Inert atmosphere

With lithium aluminium tetrahydride; cobalt(II) chloride hexahydrate; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: Mitsunobu reaction / 6.2: Mitsunobu reaction;

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

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

tiolacetic acid

Downstream raw materials:

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