(2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester
• CAS No.: 252847-74-8
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• Mol file: 252847-74-8.mol

Synonyms:(2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester

Chemical Property of (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester

There total 1 articles about (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester 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: 57.0%

methanol (67-56-1) + [(2R,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine] (207129-35-9) → (2R,4S,5R)-1-azabicyclo[2.2.2]octane-2,5-dicarboxylic acid dimethyl ester + (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester (252847-74-8)

Guidance literature:

[(2R,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine]; With potassium permanganate; sulfuric acid; In water; at 20 ℃; for 5h;

methanol; With hydrogenchloride; at 20 ℃; for 120h; Further stages.;

DOI:10.1021/ol990981o

Reference yield: 91.0%

(2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester (252847-74-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,4S,5R)-2-(tert-butyl(diphenyl)silyloxy)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester (252847-81-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/ol990981o

Reference yield:

(2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester (252847-74-8) → C17H34N2O3SiC10H4

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / triethylamine; DMAP / CH₂Cl₂ / 14 h / 20 °C

2: 65 percent / Me₂AlCl / CH₂Cl₂ / 0 - 20 °C

With dmap; dimethylaluminum chloride; triethylamine; In dichloromethane;

DOI:10.1021/ol990981o

upstream raw materials:

methanol

[(2R,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine]

Downstream raw materials:

(2R,4S,5R)-2-(tert-butyl(diphenyl)silyloxy)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester