Hydrochloric Acid → HCID 21968278, compound

Participants

Reaction Conditions

Reaction Steps

Borane-THF complex (1:1) (400 ml) was transferred into a 4 necked flask with a syringe (under N2 flow). This solution was cooled to 0° C. A solution of 2,3,4,5-tetra-hydro-2-(phenylmethyl)-1H-pyrido[4,3-b]indole (52.5 g), prepared as described in J. Med. Chem. 9:436-438 (1966), in THF (400 ml) was added over a 1 hour period at 0-5° C. The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was stirred and refluxed for 4 hours, then cooled to room temperature. 6N HCl (300 ml) was added. The organic solvent was removed by evaporation. Dioxane (400 ml) was added to the residue and the mixture was stirred and refluxed for 1 hour. The solvent was evaporated. Water (300 ml) was added to the residue and this mixture was alkalized with a diluted NaOH solution. This mixture was extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue (20 g) was crystallized from DIPE (100 ml). The crystals were filtered off and dried, yielding 7.5 g (14%) of (±)-trans-1,3,4,4a,5,9b-hexahydro-2-(phenylmethyl)-2H-pyrido[4,3-b]indole (intermediate 13).

Provenance & Evidence