Water → HCID 60762221, compound

Reaction equation

[BH4-].[Na+].[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][N:12]([CH2:19][CH2:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)C(=O)C(F)(F)F)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].O>C(O)C>[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][NH:12][CH2:19][CH2:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

Procedure

102 mg of sodium borohydride (2.7 mmol) were added to a solution of 260 mg of N-(4-tert-butyl-benzyl)-2,2,2-trifluoro-N-[2-(4-methyl-thiazol-2-yl)-ethyl]-acetamide (0.68 mmol) in ethanol at ambient temperature and the reaction mixture was stirred for 3 h. Then water was added and the mixture was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered and the solvent was evaporated. The remaining 195 mg (100%) of (4-tert-butyl-benzyl)-[2-(4-methyl-thiazol-2-yl)-ethyl]-amine were used in the following coupling step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.31 (s, 9H), 2.41 (s, 3H), 3.06 (m, 2H), 3.17 (m, 2H), 3.81 (s, 2H), 6.72 (s, 1H), 7.25 (d, J=8 Hz, 2H), 7.34 (d, J=8 Hz, 2H); MS (ISP) 289.1 (M+H)+.