(2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

Base Information

Chemical Name:(2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
CAS No.:890022-42-1
Molecular Formula:C₂₀H₂₆BrNO₄
Molecular Weight:424.335
Hs Code.:

Synonyms:(2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

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Chemical Property of (2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

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Technology Process of (2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

There total 1 articles about (2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl 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: 85.0%

: 103935-47-3
2-bromoethyl triflate

: (4S)-benzyl-(2S)-tert-butyl-5-oxooxazolidine-3-carboxylic acid allyl ester

: 890022-42-1
(2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

Guidance literature:: (4S)-benzyl-(2S)-tert-butyl-5-oxooxazolidine-3-carboxylic acid allyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

2-bromoethyl triflate; In tetrahydrofuran; toluene; at -78 - 20 ℃;
DOI:10.1016/j.bmc.2006.01.031

Reference yield: 82.0%

: 890022-42-1
(2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

: 2812-46-6
proline tert-butyl ester

: 890022-43-2
4-benzyl-4-[2-(2-tert-butoxycarbonyl-pyrrolidin-1-yl)-ethyl]-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 72h;
DOI:10.1016/j.bmc.2006.01.031

Reference yield:

: 890022-42-1
(2S,4R)-4-Benzyl-4-(2-bromo-ethyl)-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

: ((S)-1-{(R)-1-Benzyl-3-[(S)-2-((S)-1-tert-butylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-formyl-propylcarbamoyl}-2-methyl-propyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / Et₃N / dimethylformamide / 72 h / 60 °C

2: 50 percent / LiAlH₄ / tetrahydrofuran / 48 h / -78 °C

3: 83 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

4: 67 percent / HOBt; DCC / tetrahydrofuran / 0 - 20 °C

5: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 24 h / 20 °C

6: 485 mg / HOAT; Et₃N; CIP / CH₂Cl₂ / 0 - 20 °C

7: 47 percent / HgO; BF₃*Et₂O / tetrahydrofuran; H₂O / 2 h

With lithium aluminium tetrahydride; 1-hydroxy-7-aza-benzotriazole; boron trifluoride diethyl etherate; benzotriazol-1-ol; dimedone; triethylamine; dicyclohexyl-carbodiimide; mercury(II) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.01.031