Hydrogen Bromide → HCID 67594446, compound

Participants

Reaction Steps

A solution of 4,5α-epoxy-3,14-dimethoxy-5-methylmorphinan-6-one hydrochloride (H. Schlnidhammer et al., Helv. Chim. Acta Vol. 77: 1585-1589, 1994) (1.0 g, 2.73 mmol) in 3.5 ml of 48% HBr was refluxed for 15 min. After cooling, the now brown solution was evaporated, the residue treated with MeOH and again evaporated (this operation was repeated once). The oily residue was crystallized from MeOH to yield 713 mg (66%) of colorless 4,5a-epoxy-3-hydroxy-14-methoxy-5-methylmorphinan-6-one hydrobromide (compound 6). M.p.>230° C. (dec.). IR (KBr): 3545 and 3495 (+NH, OH), 1720 (CO)cm-1. CI-MS:m/z 316(M+ +1). 1H-NMR(DMSO-d6):δ9.37 (s, OH), 8.65 (broad s, +NH2), 6.64 (dd, J=8.2, 8.2 Hz, 2 arom. H), 3.36 (s, OCH3 --C(14)), 1.48 (s, CH3 --C(5)). Analysis calculated for C18H21NO4. HBr. MeOH(428.33):C 53.28, H 6.12, N 3.27; found: C 53.12, H 5.97, N 3.32.

Provenance & Evidence