Potassium Carbonate → (1S,2S)-2-amino-1-((R)-1-benzhydrylpiperidin-2-yl)-3-(3,5-difluorophenyl)propan-1-ol

온도

100 °C

Step I (7): Preparation of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-1-benzhydrylpiperidin-2-yl)oxazolidin-2-one. To a solution of (4S,5R)-4-(3,5-difluorobenzyl)-5-((R)-piperidin-2-yl)oxazolidin-2-one (Step I (6), 70 mg, 0.24 mmol) in acetonitrile (1.8 mL) were added potassium carbonate (50 mg, 0.36 mmol) and bromodiphenylmethane (90 mg, 0.36 mmol). The reaction mixture was then heated to 100° C. for 30 min using microwave heating. The solvent was removed and the crude mixture was purified by silica gel Flash Chromatography to give 60 mg of the title compound (50% yield): 1H NMR (CDCl3, 500 MHz) δ 1.28 (1H, brd s), 1.56-1.83 (4H, m), 1.94 (1H, m), 2.13 (1H, t, J=10 Hz), 2.67 (1H, m), 2.77 (1H, m), 2.88 (1H, m), 3.16 (1H, t, J=5 Hz), 3.81 (1H, m), 4.95 (1H, s), 5.10 (1H, s), 5.14 (1H, m), 6.54 (2H, m), 6.69 (1H, m), 7.18-7.27 (4H, m), 7.32-7.38 (4H, m), 7.42 (2H, d, J=10 Hz). MS (ESI) (M+Na)+ 485.12.

1. temperatureheating
2. customThe solvent was removed
3. customthe crude mixture was purified by silica gel Flash Chromatography

ORD 기록

ord-d7c8cea54a114143ac46c23a900c790b

출처 데이터셋

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07388007B2