Hydrochloric Acid → HCID 22500572, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) suspension of the product of step b (1.49 g, 3.65 mmol) in methanol (36 ml) was added portionwise sodium borohydride (270 mg, 7.30 mmol) and the resultant suspension stirred at this temperature for 20 minutes. The suspension was allowed to warm to 0° C. and the reaction stirred for a further 30 minutes. The suspension was treated with aqueous 2M hydrochloric acid (3.6 ml) and the stirring was continued for a further 1 h. The reaction mixture was treated with sufficient aqueous 2M sodium hydroxide to pH 11 and water (100 ml) was added. The aqueous phase was extracted thrice with DCM (100 ml) and the combined organic extracts were dried over anhydrous sodium sulfate. The filtrate was evaporated at reduced pressure and the residue was dissolved in methanol (10 ml) and treated with palladium on charcoal (150 mg). The resultant suspension was stirred under a hydrogen atmosphere (via balloon) for 16 h. The suspension was filtered through a pad of celite and the filter-cake was washed with methanol (100 ml). The filtrate was evaporated at reduced pressure and the residue was purified by flash column chromatography (90:10:1 DCM:methanol:ammonia) to obtain the title compound (437 mg, 42%). 1H NMR 7.87-7.82 (2H, m), 7.74-7.69 (2H, m), 3.72-3.65 (2H, m), 2.89-2.82 (2H, m), 2.28 (3H, s), 1.89-0.84 (1H, m).

Provenance & Evidence