1-Azatricyclo(3.3.1.1,3,7)decan-4-one → HCID 178419232, compound

Temperature

-78 °C

1-azatricyclo[3.3.1.13,7]decan-4-one (prepared as described in Becker, D. P., Flynn, D. L. Synthesis 1992, 1080-1082) (1.54 g, 10.2 mmol) was dissolved in acetone (10 mL) and the mixture was chilled to −78° C. To the reaction mixture was added a solution of borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 11 mL, 11 mmol). The reaction was stirred at −78° C. for 1 hour. The reaction was then diluted with water (50 mL) and extracted with CHCl3 (3×50 mL). The organic extracts were combined and washed with brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (5% ethyl acetate in CH2Cl2, Rf=0.44) to afford the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ 1.13-1.85 (br m, 3H; BH3), 2.08-2.23 (m, 5H), 2.61 (s, 2H), 3.32-3.44 (m, 6H) ppm. MS (DCI/NH3) m/z 181 (M+NH3—H)+.

1. extractionextracted with CHCl3 (3×50 mL)
2. washwashed with brine (50 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by silica gel chromatography (5% ethyl acetate in CH2Cl2, Rf=0.44)

ORD record

ord-25ffa98c02e94d7b8b370f4f1d2830ac

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163914B2