Tryptophol → HCID 44238076, compound

Participants

Reaction Steps

The more polar 4-dimethylamino-2-fluoro-4-phenylcyclohexanone (950 mg, 4.04 mmol) together with tryptophol (723 mg, 4.04 mmol) was dissolved in absolute dichloromethane (45 ml) at 0° C. (inside temperature). Trimethylsilyl triflate (987 mg, 4.44 mmol, 0.81 ml, 1.225 g/ml) was then added quickly in drops to absolute dichloromethane (10 ml). The reaction mixture immediately changed colour from yellow to red-brown. The reaction mixture was stirred for 5 h at room temperature and became cloudy during this. 5N sodium hydroxide solution (60 ml) was added to the reaction mixture and stirred for 10 min. A colourless solid separated out of the two-phase mixture. This was filtered off by means of a fritted glass filter and then washed with methanol (50 ml). The solid was the more polar diastereoisomer (241 mg). The more polar diastereoisomer was separated from the filtrate again and filtered off once again. After phase separation the aqueous phase was extracted with dichloromethane (4×40 ml). The combined organic phases were dried over sodium sulphate, filtered and then completely freed of volatile constituents in a vacuum. An attempt was made to separate the residue by chromatography [silica gel (150 g), chloroform/ethanol 19:1 (1000 ml), methanol (500 ml)]. 676 mg (1.70 mmol, 42%, mp 260-265° C.) of a more non-polar diastereomer and a total of 572 mg (1.44 mmol, 36%, mp 237-242° C.) of the more polar diastereoisomer were isolated.

Provenance & Evidence