Water → HCID 68539805, compound

Participants

Reaction Steps

To a 100 ml round-bottom flask containing a solution of (6aR,9R)-7-Cyano-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester (1.57 g, 5.35 mmol) in acetic acid (20 ml) is added water (4 ml) and zinc (1.5 g). The reaction mixture is refluxed at 100° C. for 3 hours by which time TLC in 20% methanol/DCM showed conversion of starting material to give product as a mixture of diastereomers. The reaction mixture is filtered to remove the zinc and the filter paper is washed thoroughly with water (200 ml) and ethyl acetate (200 ml). The aqueous phase is made basic with the addition of solid sodium hydrogen carbonate. The phases are then extracted and allowed to separate. The aqueous phase is re-extracted with ethyl acetate (2×100 ml) and the combined organic phases washed with brine (200 ml), dried (MgSO4), filtered at the pump and concentrated in vacuo to give a beige coloured foam. Purification is carried out by Normal Phase Flash column chromatography (Biotage Flash 40, 40 g cartridge) using 10% methanol/dichloromethane to achieve separation. Product is isolated as a beige foam.

Provenance & Evidence