Methyl benzilate → 1-Benzyl-3-pyrrolidinyl hydroxy(diphenyl)acetate

反応式

[C:1]([O:17][CH3:18])(=[O:16])[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:19]([N:26]1[CH2:30]C[CH:28](O)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCCCCC.[H-].[Na+]>[CH2:19]([N:26]1[CH2:27][CH2:28][CH:18]([O:17][C:1](=[O:16])[C:2]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[OH:3])[CH2:30]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

実験手順

To a solution of 12 g methyl benzilate and 8.2 g 1-benzyl-3-pyrrolidinol in 200 ml n-heptane is added 100 mg sodium hydride and the mixture refluxed for 4 hours, separating the methanol formed in a Dean-Stark separator. The cooled organic phase is washed with water and then extracted with 2N HCl. The aqueous phase is made alkaline with solid K2CO3 and extracted with ether to give 1-benzyl-3-(2,2-diphenyl-2-hydroxyacetoxy)pyrrolidine as an oil (18.2 g).