(2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine

Base Information

• Chemical Name: (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine
• CAS No.: 940899-66-1
• Molecular Formula: C₂₁H₂₇NO₂
• Molecular Weight: 325.451
• Mol file: 940899-66-1.mol

Synonyms:(2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine

Chemical Property of (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine

There total 12 articles about (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine 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: 84.0%

(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine (940899-62-7) → (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine (940899-66-1)

Guidance literature:

With sodium amalgam; In tetrahydrofuran; for 22h; Heating;

DOI:10.1021/jo0703101

Reference yield: 75.0%

(5S,6S)-N-benzyl-5-benzyloxy-6-methyl-2,3-dehydropiperidine-2-carbaldehyde (940899-70-7) → (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine (940899-66-1)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1021/jo0703101

Reference yield:

(5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine (940899-60-5) → (2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine (940899-66-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

2: 84 percent / NaCNBH₃; TFA / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 84 percent / sodium amalgam / tetrahydrofuran / 22 h / Heating

With sodium amalgam; tetrabutyl ammonium fluoride; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0703101

upstream raw materials:

(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

(5S,6S)-N-benzyl-5-benzyloxy-6-methyl-2,3-dehydropiperidine-2-carbaldehyde

(5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine

(5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine

Downstream raw materials:

C₂₁H₂₅NO₂