A 30312 → HCID 21968280, compound

Participants

Reaction Steps

A mixture of 2,3,4,5-tetrahydro-8-methoxy-2-(phenylmethyl)-1H-pyrido[4,3-b]indole monohydrochloride (39.5 g), prepared as described in J. Org. Chem. 44:1063-1068 (1979), in 2-methoxyethyl ether (250 ml) was stirred and cooled in an ice bath, under a N2 flow. Sodium borohydride (11.7 g, solid) was added in 8 portions. The mixture was stirred overnight at room temperature, then cooled to 5° C. Ice water (500 ml) was added dropwise. Precipitation resulted. The mixture was stirred for 2 hours. The precipitate was filtered off. 1,4-Dioxane (350 ml) was added and the mixture was stirred. HCl (200 ml, 12N) was slowly added and the mixture was heated to reflux temperature. The mixture was stirred and refluxed for 1 hour, then cooled and the solvent was evaporated. The residue was stirred in water (300 ml) and this mixture was alkalized with an aqueous NaOH solution. The mixture was stirred for 1 hour. The mixture was extracted with DCM (2×200 ml). The combined extracts were dried, filtered and the solvent was evaporated. The residue was dissolved in DIPE (300 ml), then filtered and the filtrate was evaporated, yielding 11.3 g (32%) of (±)-trans-2,3,4,4a,5,9b-hexahydro-8-methoxy-2-(phenylmethyl)-1H-pyrido[4,3-b]indole (intermediate 8).

Provenance & Evidence