Ammonia → HCID 69269014, 화합물

반응식

C[O:2][C:3](=O)[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[CH:7]=1)=[O:5].CO.[BH4-].[Na+].[NH3:33]>>[CH2:21]([N:18]1[CH2:17][CH2:16][CH:15]([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([CH:4]([OH:5])[C:3]([NH2:33])=[O:2])=[CH:7]2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

반응물 4

HCID 222Ammonia

HCID 887Methanol

HCID 4311764Sodium borohydride

HCID 69269504HCID 69269504, 화합물

생성물 1

HCID 69269014HCID 69269014, 화합물수율 103%

실험 절차

Dissolve [1-(1-benzylpiperidin-4-yl)-1H-indol-3-yl]oxoacetic acid methyl ester (1.29 g, 3.43 mmol) in 2 M ammonia: methanol (35 mL) and stir at room temperature under nitrogen for 1.5 hours. Concentrate to a white solid and slurry into absolute ethanol (40 mL). Add sodium borohydride (0.65 g, 5 equiv) and stir 3 hours at room temperature under nitrogen. Concentrate then dilute with ethyl acetate and quench with water. Wash organic layer with brine. Dry over magnesium sulfate, filter and concentrate to give crude product (1.28 g, 103%). MS (ES, m/z): 364.2 (M+1).