(1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

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Chemical Name:(1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate
CAS No.:908005-82-3
Molecular Formula:C₁₆H₃₀BrNO₂Si
Molecular Weight:376.409
Hs Code.:

Synonyms:(1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

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Chemical Property of (1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

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Technology Process of (1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

There total 1 articles about (1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate 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:

: 86953-79-9
tert-butyl pyrrolidine-1-carboxylate

: 86994-20-9
(E)-4-bromo-1-iodo-1-(trimethylsilyl)-1-butene

: 908005-82-3
(1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

: (1,1-dimethylethyl)-(S)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

Guidance literature:: tert-butyl pyrrolidine-1-carboxylate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; at -78 ℃; for 1h;

With tributylphosphine; neophyl lithium; In diethyl ether; at -78 ℃; for 0.5h;

(E)-4-bromo-1-iodo-1-(trimethylsilyl)-1-butene; In diethyl ether; at -78 ℃; for 1h; Title compound not separated from byproducts;
DOI:10.1021/jo060717q

Reference yield:

: 908005-82-3
(1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate

: 33023-01-7
(+)-elaeokanine A

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / Me₃SiXl / methanol / 25 °C

2.1: aq. HBr; NaBr; NBS / diethyl ether / 0.5 h / 0 - 20 °C

2.2: 67 percent / H₂SiF₆ / diethyl ether / 12 h / 20 °C

3.1: t-BuLi / tetrahydrofuran / 1 h / -78 °C

3.2: 60 percent / tetrahydrofuran / 2 h / 20 °C

With N-Bromosuccinimide; Me₃SiXl; hydrogen bromide; tert.-butyl lithium; sodium bromide; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/jo060717q