Hydrochloric Acid → HCID 66905238, compound

Participants

Reaction Steps

To a suspension of trans-7-amino-6-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide hydrochloride (229.3 mg, 0.81 mmol) in a mixture of dichloromethane (2.0 mL) and methanol (0.3 mL) was added N,N-diisopropyl-ethylamine (0.10 g, 0.80 mmol) followed by tort-butyl (4S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (0.18 g, 0.80 mmol). Sodium triacetoxyborohydride (0.20 g, 0.97 mmol) was added and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated to dryness and dissolved in ethyl acetate (40 mL). The suspension was washed with saturated sodium bicarbonate (15 mL) and brine (15 mL), dried over sodium sulfate, filtered and concentrated to give a white foam. The white foam was treated with AcOH (1.0 mL) and 6N HCl (1.0 mL) at 70° C. for 1 h. The reaction mixture was concentrated, and evaporated with ethyl acetate (3×2 mL) to give the hydrochloride salt of the title compound as a dark greenish powder (304 mg, 96% yield). (m/z): [M+H]+ calcd for C17H27N3O3, 322.21; found, 322.2.

Provenance & Evidence