Diisobutylaluminum hydride → HCID 90409078, compound

Temperature

-78 °C

To a −78° C. solution of 2-(1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetaldehyde (150 mg, 0.465 mmol) in DCM (5 mL) under N2 was added dropwise DIBAL-H (0.558 mL of a 1 M solution in DCM, 0.558 mmol). The reaction mixture was stirred at −78° C. for 2 h, after which CELITE® (3500 mg) was added. The reaction was then quenched at −78° C. with sat. aq. NH4Cl (2 mL). The mixture was stirred at rt for 30 min, after which MgSO4 (1000 mg) was added. Stirring was continued at rt for 1 h, after which the mixture was filtered. The solid was washed with DCM (4×). The combined filtrates were concentrated in vacuo to give a crude oil, which was purified by flash chromatography (SiO2) using a gradient from 0% to 50% EtOAc/hexane (10 min) to give the title compound (135 mg, 0.416 mmol, 89% yield) as a clear oil. 1H NMR (CDCl3) δ: 7.78-7.73 (dd, J=7.9, 1.9 Hz, 1H), 7.38-7.32 (m, 2H), 7.20-7.07 (m, 3H), 7.01-6.95 (m, 2H), 6.83-6.78 (dd, J=8.0, 1.4 Hz, 1H), 3.96-3.84 (s, 2H), 3.75-3.66 (t, J=7.4 Hz, 2H), 2.61-2.50 (m, 2H), 1.98-1.88 (m, 2H), 1.75-1.61 (m, 4H), 1.51-1.42 (t, J=7.4 Hz, 2H), 1.33 (s, 1H).

1. additionafter which CELITE® (3500 mg) was added
2. customThe reaction was then quenched at −78° C. with sat. aq. NH4Cl (2 mL)
3. stirringThe mixture was stirred at rt for 30 min
4. additionafter which MgSO4 (1000 mg) was added
5. stirringStirring
6. waitwas continued at rt for 1 h
7. filtrationafter which the mixture was filtered
8. washThe solid was washed with DCM (4×)
9. concentrationThe combined filtrates were concentrated in vacuo
10. customto give a crude oil, which
11. customwas purified by flash chromatography (SiO2)
12. customfrom 0% to 50% EtOAc/hexane (10 min)

ORD record

ord-104a912ab5ea47f5bad5de9c7ac316b9

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962660B2