Borane;tetrahydrofuran → 4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol

To a solution of 4-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanoic acid (115 mg, 0.307 mmol) in dry THF (1 mL) at 0° C. under N2 was added BH3.THF (0.461 ml, 0.461 mmol) over a period of 3 min. The resulting mixture was stirred at 0° C. for 30 min and at room temperature 3 h. The reaction was cooled to 0° C. and quenched with water carefully. The mixture was extracted with ethyl acetate. The organic layer was washed with sat′d aqueous NaHCO3, water, dried, and the concentrated in vacuo to afford the title compound (111 mg, 100% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.23 (t, J=8.0 Hz, 1H), 7.14-7.11 (m, 1H), 7.04-7.00 (m, 1H), 6.94 (ddd, J=8.2, 2.5, 0.8 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 3.98-3.91 (m, 1H), 3.83 (s, 2H), 3.67 (t, J=6.5 Hz, 2H), 3.64-3.58 (m, 1H), 2.04 (t, J=7.8 Hz, 5H), 1.90-1.83 (m, 2H), 1.75-1.50 (m, 10H), 1.38-1.26 (m, 2H), 1.22-1.15 (m, 2H).

1. temperatureThe reaction was cooled to 0° C.
2. customquenched with water carefully
3. extractionThe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with sat′d aqueous NaHCO3, water
5. customdried
6. concentrationthe concentrated in vacuo

ORD record

ord-dbd3894c13f94b798e8f920fbd09e89b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962660B2