Water → HCID 21835802、化合物

反応式

[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13](=[O:35])[C:14]([F:34])([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:13]([OH:35])[C:14]([F:34])([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

参加物

反応条件

温度: 0 °C

実験手順

Sodium borohydride (20 mg, 0.53 mmol) is added to a solution of ethyl 1-(p-chlorophenyl)-α-fluoro-β-oxo-α-(m-phenoxybenzyl)cyclopropanepropionate (214 mg, 0.46 mmol) in methanol at 0° C. The reaction mixture is stirred at 0° C. for 20 minutes, treated with water (2 mL), and concentrated in vacuo to obtain a residue. A solution of the residue in ethyl acetate is washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a colorless gum (224 mg, 100%) which is found to have a 9:1 [R,S and S,R] to [R,R and S,S] ratio by NMR spectral analyses.