Sodium Hydroxide → HCID 86743886, compound

Participants

Reaction Steps

Methyl 5-[3-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]hexyl]oxy]propyl]-3-pyridineacetate (800 mg) in benzene (10 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (95 mg) in ether (10 ml) at 0° C. The mixture was stirred overnight at room temperature under nitrogen, and more lithium aluminum hydride (40 mg) was added. After being stirred for a further 3 h, the mixture was treated with water (1 ml), followed by 2N sodium hydroxide (1 ml) and water (3 ml). The suspension was filtered through hyflo and washed with ethyl acetate (3×50 ml). The combined organic extracts were dried and concentrated to give a yellow oil which was purified by FCC eluting with System A (85:5:1) to give a yellow oil. The oil (450 mg), dissolved in methanol (10 ml), was treated with fumaric acid (52 mg) and concentrated to give an oil which was triturated with ether to give the title compound as a yellow solid (420 mg), m.p. 85°-86° C.

Provenance & Evidence