(4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

Base Information

Chemical Name:(4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine
CAS No.:136630-88-1
Molecular Formula:C₁₈H₂₆BrNO₃
Molecular Weight:384.313
Hs Code.:

Synonyms:(4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

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Chemical Property of (4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

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Technology Process of (4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

There total 5 articles about (4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine 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: 78.0%

: 136630-86-9
(2R,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol

: 77-76-9
2,2-dimethoxy-propane

: 136630-88-1
(4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; for 14h; Ambient temperature;
DOI:10.1021/jm00115a016

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 136630-88-1
(4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: N-methylmorpholine (NMM) / ethyl acetate / 0.17 h / -10 °C

2: diethyl ether / 3 h / Ambient temperature

3: 47percent aq. HBr / dioxane / 1 h / 0 °C

4: 70 percent / lithium tri-(tert-butoxy)aluminum hydride / diethyl ether / 0.5 h / Ambient temperature

5: 78 percent / p-toluenesulfonic acid / CH₂Cl₂ / 14 h / Ambient temperature

With 4-methyl-morpholine; lithium tri-(tert-butoxy)aluminum hydride; hydrogen bromide; toluene-4-sulfonic acid; In 1,4-dioxane; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jm00115a016

Reference yield:

: 60398-41-6
(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate

: 136630-88-1
(4S,5R)-4-benzyl-5-(bromomethyl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 47percent aq. HBr / dioxane / 1 h / 0 °C

2: 70 percent / lithium tri-(tert-butoxy)aluminum hydride / diethyl ether / 0.5 h / Ambient temperature

3: 78 percent / p-toluenesulfonic acid / CH₂Cl₂ / 14 h / Ambient temperature

With lithium tri-(tert-butoxy)aluminum hydride; hydrogen bromide; toluene-4-sulfonic acid; In 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1021/jm00115a016