2-Butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester → 2-Butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]([C:15]1[CH:20]=[CH:19][C:18]([N:21]([Si:26]([CH3:29])([CH3:28])[CH3:27])[Si:22]([CH3:25])([CH3:24])[CH3:23])=[C:17]([Cl:30])[CH:16]=1)[OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:31][CH2:32][CH2:33][CH3:34])[C:13](=[O:14])[C:15]1[CH:20]=[CH:19][C:18]([N:21]([Si:26]([CH3:27])([CH3:29])[CH3:28])[Si:22]([CH3:25])([CH3:24])[CH3:23])=[C:17]([Cl:30])[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]参加物
3
反応物 1
生成物 1
試薬・触媒・溶媒 1
実験手順
To a stirred solution of 2-butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.357 g, 0.678 mmol) in DCM (10 mL) at ambient temperature under nitrogen was added DMP (0.575 g, 1.36 mmol) in a single portion. After one hour the reaction mixture was diluted with DCM, washed with 1 N NaOH and brine, then dried (MgSO4), filtered and concentrated in vacuo to a brown residue (0.290 g). Purification by chromatography (silica, 10% EtOAc in hexanes) gave 2-butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.208 g, 0.397 mmol, 58%) as a clear colourless residue.