Triethylamine → HCID 59536873, compound

Participants

Reaction Conditions

Reaction Steps

Of the compound from Example 82A, 430 mg (1.29 mmol) were suspended in 5 ml of THF and cooled to 0° C., and the suspension was admixed with 179 μl (1.29 mmol) of triethylamine and also with 184 μl (1.42 mmol) of isobutyl chloroformate and stirred at 0° C. for 1 hour. The suspension was then filtered through a Seitz frit into a cooled flask, and the retained solid was washed with a little THF. The filtrate was added slowly dropwise, with ice cooling, to a solution of 146 mg (3.86 mmol) of sodium borohydride in 0.5 ml of water and stirred at 0° C. for 1 h. For work-up, the reaction mixture was admixed with about 10 ml of saturated aqueous sodium hydrogen carbonate solution and extracted with 50 ml of ethyl acetate. The organic phases were washed once with saturated aqueous sodium hydrogen carbonate solution and once with saturated aqueous sodium chloride solution. They were then dried over sodium sulphate, filtered and concentrated on a rotary evaporator. This gave 419 mg (95% of theory) of the target compound.

Provenance & Evidence