(4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 271245-79-5
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439
• Mol file: 271245-79-5.mol

Synonyms:(4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl 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: 88.0%

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + (Benzylcarbonylmethylene)triphenylphosphorane (1174-61-4) → (4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (271245-79-5)

Guidance literature:

In tetrahydrofuran; for 12h; Heating;

DOI:10.1002/jccs.200000010

Reference yield: 90.0%

(4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (271245-79-5) → (4S,3'RS)-4-(3'-hydroxy-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (271245-83-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 3h;

DOI:10.1002/jccs.200000010

Reference yield:

(4S)-4-(3'-oxo-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (271245-79-5) → (4S,1'S)-4-(1'-ethoxycarbonylmethyl-4'-phenylbutyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (271245-89-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaBH₄; CeCl₃*7H₂O / methanol / 3 h / 0 °C

2: propionic acid / 2 h / 138 °C

3: 22 percent / H₂ / 10 percent Pd/C / ethyl acetate / 12 h / 25 °C / 3102.89 Torr

With sodium tetrahydroborate; cerium(III) chloride; hydrogen; propionic acid; palladium on activated charcoal; In methanol; ethyl acetate; 1: Reduction / 2: Rearrangement / 3: Catalytic hydrogenation;

DOI:10.1002/jccs.200000010

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(Benzylcarbonylmethylene)triphenylphosphorane

Downstream raw materials:

(4S,3'RS)-4-(3'-hydroxy-4'-phenylbut-1'(E)-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(5S)-N-(tert-butoxycarbonyl)-(4R)-(3'-phenylpropyl)-tetrahydropyran-2-one

(5S)-N-(tert-butoxycarbonyl)-(4S)-(3'-phenylpropyl)-tetrahydropyran-2-one

(4S,1'R)-4-(1'-ethoxycarbonylmethyl-4'-phenylbutyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester