Ammonia → HCID 69269014, Verbindung

Reaktionsgleichung

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

Komponenten

Edukt 4

HCID 222Ammonia

HCID 887Methanol

HCID 4311764Sodium borohydride

HCID 69269504HCID 69269504, Verbindung

Produkt 1

HCID 69269014HCID 69269014, VerbindungAusbeute 103 %

Versuchsvorschrift

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).