Hydrogen Peroxide → HCID 23294136, compound

Temperature

0 °C

To a round bottom flask was added 2-benzyl-2-azabicyclo[2.2.1]hept-5-ene (1 g, 5.40 mmol) and THF (7 mL). The reaction was cooled to 0° C. and 1N BH3.THF (10.80 mL, 10.80 mmol) was slowly added to the reaction. The reaction was stirred at 0° C. for 1 hr and then water (0.5 ml) was added to the reaction dropwise to quench the excess BH3. 1N NaOH (5.94 mL, 5.94 mmol) and 30% H2O2 (0.182 mL, 5.94 mmol) were added to the reaction and the reaction was stirred at 40° C. for 1 hr. The reaction was cooled to rt and K2CO3 (1 g) was added. The reaction was diluted with CH2Cl2 (50 ml) and washed with water (2×20 ml) and saturated aqueous NaCl (30 ml). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by RP prep-HPLC. The major peak was collected and fractions were concentrated to give 2-benzyl-2-azabicyclo[2.2.1]heptan-6-ol (850 mg, 4.18 mmol, 77% yield). Anal. Calcd. for C13H17NO m/z 203.3, found: 204.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.48-7.32 (m, 5 H), 4.47 (d, J=6.60 Hz, 1 H), 4.29 (br. s., 1 H), 4.23-4.05 (m, 2 H), 3.78 (s, 1 H), 3.29 (dd, J=11.00, 4.40 Hz, 1 H), 2.81-2.72 (m, 1 H), 2.68 (br. s., 1 H), 2.09 (d, J=11.55 Hz, 1 H), 2.04-1.95 (m, 1 H), 1.77 (d, J=12.10 Hz, 1 H), 1.60-1.50 (m, 1 H); 13C NMR (126 MHz, CDCl3) δ ppm 130.61, 130.04, 129.42, 68.31, 67.72, 59.17, 58.03, 37.98, 35.49, 31.24.

1. customto quench the excess BH3
2. stirringthe reaction was stirred at 40° C. for 1 hr
3. temperatureThe reaction was cooled to rt
4. washwashed with water (2×20 ml) and saturated aqueous NaCl (30 ml)
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by RP prep-HPLC
9. customThe major peak was collected
10. concentrationfractions were concentrated

ORD record

ord-b622a63971c342759570be8be5dd86f3

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815909B2