Sodium borohydride → 2-(2,6-dichloro-4-fluorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine

関与物質

反応手順

A mixture of 1-methylcyclopropanecarbaldehyde (31.6 mg, 0.375 mmol) and 2-(2,6-dichloro-4-fluorophenyl)-2-((triethylsilyl)oxy)ethanamine (127 mg, 0.375 mmol) in MeOH (1.9 ml) was stirred at room temperature for 3 h. NaBH4 (14.20 mg, 0.375 mmol) was added in portions and the mixture was stirred at room temperature for 40 min. The mixture was concentrated and purified by prep TLC eluted with 5% MeOH/DCM to provide 2-(2,6-dichloro-4-fluorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine (111 mg, 0.273 mmol, 72.8% yield). 1H NMR (500 MHz, CDCl3) δ 7.29 (s, 1H), 7.06-7.10 (m, 2H), 5.56 (br. s., 1H), 3.33 (t, J=10.51 Hz, 1H), 2.81 (d, J=9.17 Hz, 1H), 2.60-2.67 (m, 1H), 2.44 (d, J=11.86 Hz, 1H), 1.46-1.59 (m, 1H), 1.13 (s, 3H), 0.85-0.96 (m, 9H), 0.50-0.63 (m, 6H), 0.36 (br. s., 2H), 0.30 (br. s., 2H); LCMS (ESI) m/z 406.0 (M+H)+.

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