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

HRID 1855048Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1.B.C1COCC1>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:9]=[C:10]([C:14]23[CH2:19][CH2:18][C:17]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])([CH2:20][CH2:21]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-dbd3894c13f94b798e8f920fbd09e89b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962660B2

Reaction notes

Loading…