benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate
• CAS No.: 1227685-18-8
• Molecular Formula: C₁₅H₁₈Cl₃NO₃
• Molecular Weight: 366.672
• Mol file: 1227685-18-8.mol

Synonyms:benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate

Chemical Property of benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate

There total 9 articles about benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-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: 48.0%

benzyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate (921599-74-8,852051-10-6) + chloroform (67-66-3,8013-54-5) → benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate (1227685-18-8)

Guidance literature:

With magnesium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; at -77 - -15 ℃; Cooling with acetone-dry ice;

Reference yield:

benzyl (2S,4S)-2-methyl-4-(trichloromethyl)-4-[(trimethylsilyl)oxy]piperidine-1-carboxylate → benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate (1227685-18-8)

Guidance literature:

benzyl (2S,4S)-2-methyl-4-(trichloromethyl)-4-[(trimethylsilyl)oxy]piperidine-1-carboxylate; With tetrabutyl ammonium fluoride; acetic acid; In 2-methyltetrahydrofuran; at 20 ℃; for 0.5h;

With potassium carbonate; In 2-methyltetrahydrofuran; water;

Reference yield:

3,4-dihydro-2-methyl-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester (190906-91-3) → benzyl (2S,4S)-4-hydroxy-2-methyl-4-(trichloromethyl)-piperidine-1-carboxylate (1227685-18-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / zinc / 3 h / 60 °C

2.1: Chiralpak AD / methanol

3.1: lithium hexamethyldisilazane / tetrahydrofuran / -70 - -20 °C

3.2: 12 h / -5 - 5 °C

4.1: tetrabutyl ammonium fluoride; acetic acid / 2-methyltetrahydrofuran / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; acetic acid; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; 2-methyltetrahydrofuran; methanol;

upstream raw materials:

benzyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate

chloroform

3,4-dihydro-2-methyl-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester

benzyl chloroformate

Downstream raw materials:

(2S,4R)-1-benzyl 4-methyl 4-(3-fluorophenylamino)-2-methylpiperidine-1,4-dicarboxylate

(2S,4R)-1-benzyl 4-methyl 4-azido-2-methylpiperidine-1,4-dicarboxylate

benzyl (2S,4R)-4-cyano-4-[(3-ethoxy-3-oxopropanoyl)(3-fluorophenyl)amino]-2-methylpiperidine-1-carboxylate

benzyl (5R,7S)-1-(3-fluorophenyl)-4-hydroxy-7-methyl-2-oxo-1,8-diazaspiro[4.5]decane-8-carboxylate