N-(tert-Butoxycarbonyl)-D-prolinal → tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate

HRID 81397

反応式

HRID 81397 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5]P(=O)(OCC)OCC.C[Si](C)(C)N[Si](C)(C)C.[Li].[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH2:36][C@@H:35]1[CH:39]=O)=[O:33])([CH3:30])([CH3:29])[CH3:28]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:39]/[C@H:35]2[CH2:36][CH2:37][CH2:38][N:34]2[C:32]([O:31][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:33])[CH:14]=[CH:15][CH:16]=1

参加物

5

実験手順

775 mg of commercially available diethyl 3-chlorobenzylphosphonate are dissolved in 20 ml of THF, and 3 ml of lithium hexamethyldisilazane are added dropwise at −78° C. under protective gas. After 1 h, a solution of 500 mg of tert-butyl-(R)-2-formylpyrrolidine-1-carboxylate in 5 ml of THF is added dropwise at the temperature indicated. The batch is stirred at RT for 3 h and subsequently subjected to aqueous work-up, giving 1 g of tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate as colourless oil, which is immediately reacted further.

出典と根拠

ORDレコード
ord-fcfd28a2209f4e4eae364783af707dc1
出典データセット
uspto-grants-2014_09
特許番号
US08846694B2

関連ノート

読み込み中…