Methanol → HCID 22182534, compound

Participants

Reaction Steps

To 1,3,4,6,7,8-hexahydro-2H-5-oxa-1-aza-phenanthrene-6-carboxylic acid ethyl ester (0.80 g, 3.1 mmole) in 25 mL of tetrahydrofuran was added 0.22 g (10 mmole) of lithium borohydride. The mixture was stirred for 48 hours at room temperature. Methanol (5 mL) was added and stirring at room temperature continued for an additional hour. The mixture was then diluted to 300 mL with ethyl acetate and washed with 100 mL portions of water and saturated brine and dried over sodium sulfate. Filtration and concentration in vacuum gave 0.83 g of the title compound as a white solid. 1H-NMR (CDCl3): doublet 6.65 δ (1 H); doublet 6.1 δ (1 H); multiplet 4.1 δ (1 H); multiplet 3.8 δ (2 H); multiplet 3.2 δ (2 H); broad singlet 2.8 δ (1 H); multiplet 2.55 δ (4 H); multiplet 1.9 δ (2 H); multiplet 1.2 δ (2 H).

Provenance & Evidence