Sodium Hydroxide → 1h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-2,3-dihydro-n-(2-phenylethyl)-

HRID 855425Notes

Reaction equation

[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH2:19][CH2:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 310 mg (0.76 mmol) of 1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide in 5 ml acetic acid cooled to 0° C. were added in portions 142 mg (2.26 mmol) of sodium cyano borohydride. The reaction mixture was stirred for 2 h at 0° C. and 2N aqueous sodium hydroxide solution was added until the reaction mixture was basic. The reaction mixture was extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated to yield 310 mg (100%) of product as a colorless oil. MS (ISP) 413.5 (M+H)+.

Workup

extractionThe reaction mixture was extracted with diethyl ether
washThe combined organic layers were washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-ddc5e73ea79b46359cfbe7aeb657b852
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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