(1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide

Base Information

• Chemical Name: (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide
• CAS No.: 93454-86-5
• Molecular Formula: C₂₀H₃₅NO₃Si
• Molecular Weight: 365.588

Synonyms:(1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide

Chemical Property of (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide

Chemical Property:

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Technology Process of (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide

There total 2 articles about (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide (93454-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / imidazole / dimethylformamide / 35 °C

2: 1.)trimethylaluminum, 2.)HCl / 1.)benzene, reflux, 4 d., 2.)r.t., 30 min.

With 1H-imidazole; hydrogenchloride; trimethylaluminum; In N,N-dimethyl-formamide;

DOI:10.1021/jo00200a038

Reference yield:

(1S,2R)-(+)-ephedrine (321-98-2,7009-81-6,90-83-5,6912-63-6) + (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester (93454-85-4) → (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide (93454-86-5)

Guidance literature:

With hydrogenchloride; trimethylaluminum; Yield given. Multistep reaction; 1.)benzene, reflux, 4 d., 2.)r.t., 30 min.;

DOI:10.1021/jo00200a038

Reference yield: 80.0%

(1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-<(tert-butyldimethylsilyl)oxy>propionamide (93454-86-5) → (1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxypropionamide (93454-87-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00200a038

upstream raw materials:

(1S,2R)-(+)-ephedrine

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester

tert-butyldimethylsilyl chloride

Downstream raw materials:

(1'R,2'S,2S)-N,2-Dimethyl-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxypropionamide

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