Hydrogen Peroxide → HCID 71233132, compound

Participants

Reaction Steps

A solution of BH3-THF (1.0 M in THF)(24.5 ml, 24.5 mmol) was added dropwise to a 0° C. solution of 2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene in THF (90 mL). The reaction mixture was then stirred at rt. After 30 min the mixture was cooled to 0° C. and another 24.5 mL of BH3-THF solution was added dropwise. The mixture was then stirred at rt once again. After 30 min the mixture was cooled to 0° C. and a solution of NaOH (3.9 g in 5 ml water) was carefully added dropwise. The white slurry was stirred at 0° C. for 10 min and then a solution of 30% H2O2 (2.7 mL) was slowly added. The mixture was then stirred at rt. After 45 min concentrated NH4OH (31 mL) was added and the mixture was heated at 65° C. After 1.5 h heating was stopped. The mixture was cooled to rt and concentrated to ½ volume to remove some of the THF. The solution was then partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give the product (1R,4S)-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-6-ol (3.37 gm, 15.54 mmol, 69.7% yield) as a colorless oil. Anal. Calcd. for C14H19NO m/z 217.3, found: 218.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.40-7.17 (5 H, m), 4.03 (1 H, d, J=7.1 Hz), 3.46 (1 H, q, J=6.2 Hz), 3.01 (1 H, s), 2.51 (1 H, dt, J=8.8, 3.0 Hz), 2.37 (1 H, br. s.), 2.25 (1 H, d, J=8.8 Hz), 1.86-1.78 (1 H, m), 1.54-1.38 (3 H, m), 1.37-1.21 (4 H, m).

Provenance & Evidence