Sodium borohydride → HCID 21186580, compound

Participants

Reaction Steps

A mixture of sodium borohydride (0.16 g, 4.23 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3,5-difluoro-4-triisopropylsilyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-one (1.40 g, 2.86 mmol in 20 mL of ethanol) was added. The reaction was stirred at ambient temperature for 3 days. The reaction was quenched with water and stirred 4 h. The white precipitate which formed was collected by filtration and recrystallized from ethanol to afford 0.46 g (32%) of 1R*,2R*1-(3,5-difluoro-4-triisopropylsilyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-ol which had: NMR δ 7.54 (d, J=7.5 Hz, 2 H), 7.40 (t, J=7.5 Hz, J=8.5 Hz, 2 H), 7.31 (d, J=7 Hz, 1 H), 6.89 (d, J=9 Hz, 2 H), 5.28 (s, 1 H), 4.18 (d, J=9.5 Hz, 1 H), 3.10 (dt, J=2.2, 11.7 Hz, 1 H), 2.73-2.69 (m, 2 H), 2.62-2.51 (m, 2 H), 2.30-2.06 (m, 2 H), 1.90-1.83 (m, 2 H), 1.36-1.20 (m, 3 H), 1.10 (d, J=7 Hz, 18 H), 0.85 (d, J=6.7 Hz, 3 H). Analysis calculated for C29H43F2NO3Si: C, 67.02; H, 8.34; N, 2.69. Found: C, 66.77; H, 8.58; N, 2.71.

Provenance & Evidence