Sodium Bicarbonate → HCID 21314005, compound

Participants

Reaction Steps

5-[2-[[3-(4-Fluorophenyl)-1-methylpropyl]amino]-1-hydroxyethyl]-2-hydroxybenzoic acid, methyl ester, hydrochloride (2.66 g) was basified with 8% sodium bicarbonate solution (100 ml) and the free base was extracted into ether (3×100 ml). The dry extracts (MgSO4) were evaporated and the residual oil in tetrahydrofuran (40 ml) was added dropwise under nitrogen to a stirred solution of lithium aluminium hydride (0.74 g) in tetrahydrofuran (40 ml). When the addition was complete, the mixture was stirred at room temperature for 16 hours. The excess hydride was decomposed by the cautious addition of water (10 ml) and then the mixture was evaporated to dryness. The residue was diluted with 2 N hydrochloric acid (100 ml), basified with solid sodium bicarbonate and extracted with ether (2×50 ml). The combined extracts were dried (MgSO4) and diluted with light petroleum (b.p. 60°-80°) until turbid. The product precipitated as an off-white crystalline solid (1.21 g), m.p. 101°-103°. Recrystallization from ether-light petroleum (b.p. 60°-80°) gave colourless needles, m.p. 102°-103°.

Provenance & Evidence