Acetic Acid → HCID 18672722、化合物

反応式

[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:22]2[C:30]3[CH:29]=[C:28]4[C:31]5([CH2:37][O:38][C:27]4=[CH:26][C:25]=3[CH2:24][CH2:23]2)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]5)=[O:21])=[CH:16][CH:15]=1.[BH4-].[Na+].O.[OH-].[Na+].[C:44](O)(=O)[CH3:45]>>[CH2:44]([N:34]1[CH2:33][CH2:32][C:31]2([C:28]3[C:27](=[CH:26][C:25]4[CH2:24][CH2:23][N:22]([C:20]([C:17]5[CH:16]=[CH:15][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[N:12]=[C:11]([CH3:13])[O:10][N:9]=7)=[CH:7][C:2]=6[CH3:1])=[CH:19][CH:18]=5)=[O:21])[C:30]=4[CH:29]=3)[O:38][CH2:37]2)[CH2:36][CH2:35]1)[CH3:45]

参加物

反応物 5

HCID 176Acetic Acid

HCID 962Water

HCID 14798Sodium Hydroxide

HCID 4311764Sodium borohydride2 回

HCID 18784692HCID 18784692、化合物

生成物 1

HCID 18672722HCID 18672722、化合物収率 52%

実験手順

A stirred solution of 5-(2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E3, 100 mg, 0.20 mmole) in glacial acetic acid (2 ml) at room temperature under argon was carefully treated with sodium borohydride pellets (50 mg, 1.3 mmole) and stirred for 24 H. Additional sodium borohydride pellets were added (50 mg, 1.3 mmole) and reaction mixture stirred at room temperature for a further 72 h. The reaction mixture was then treated with water (20 ml), basified with 10% NaOH solution (20 ml) and extracted with dichloromethane. The extract was dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 3% MeOH/CHCl3. Crystallisation of the product form ethyl acetate/60-80 petrol afforded the title compound as a white solid (55 mg, 52%) mp 202-204° C.