4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

Base Information

Chemical Name:4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester
CAS No.:394734-80-6
Molecular Formula:C₂₀H₃₁NO₅
Molecular Weight:365.47
Hs Code.:

Synonyms:4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

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Chemical Property of 4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

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Technology Process of 4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

There total 3 articles about 4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-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: 34.0%

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 106-95-6
allyl bromide

: 394734-80-6
4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

: 237421-53-3
tert-butyl (2S,4S)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate

: 237421-54-4
tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate

Guidance literature:: tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;
DOI:10.1002/ejoc.201701584

Reference yield:

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 106-95-6
allyl bromide

: 394734-80-6
4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

Guidance literature:: tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -73 ℃; for 1h;

allyl bromide; In tetrahydrofuran; at 15 ℃; for 2h;

Reference yield:

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 394734-80-6
4,4-diallyl-5-oxo-pyrrolidine-1,2-(S)-dicarboxylic acid di-tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 53 percent / tetrahydrofuran / 2 h / -78 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / -78 °C

2.2: 71 percent / tetrahydrofuran / -78 °C

With lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1021/jm060077j