Ammonium Hydroxide → HCID 11729014, compound

Participants

Reaction Conditions

Reaction Steps

A 1 M solution of boron tribrornide in CH2Cl2 (7.3 ml) was added at once to an ice-cooled solution of the compound 16 (480 mg, 0.97 inmol) in 50 ml of CH2Cl2. After 50 min stirring at 0-5° C., a mixture of 13 g ice and 3 ml conc. NH4OH was added. The resulting mixture was stirred at room temperature for 30 min and the extracted with CH2Cl2 (3×30 ml). The combined organic layers were washed with brine (45 ml), dried over Na2SO4 and evaporated. The residue (204 mg slightly brown foam) was treated with 0.5 ml hot MeOH to afford 302 mg (55%) of 17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxy-5-methyl-14-n-propyloxymorphinan-6-one (compound 17). M.p. 184-186° C. IR (KBr): 3390 (OH), 1720 (CO)cm-1. CI-MS: m/z 397 (M+ +1). 1H-NMR (CDCl3): δ 10.24 (broad s, OH), 6.73 (d, J=8.2 Hz, 1 arom. H), 6.65 (d, J=8.2 Hz, 1 arom. H)1.62 (s, CH3 --C(5)), 1.00 (t,J=7.3 Hz, CH3). Analysis calculated for C24H31NO4. 0.6 MeOH (416.74): C 70.90, H 8.08, N 3.36; found: C 70.76, H 7.73, N 3.52.

Provenance & Evidence