Triethylamine → HCID 86651692, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (limiting reagent), and 4-ethylthiazole-2-carboxylic acid (1 molar equivalent) was suspended in DCM (4.5 volumes) and cooled to 16° C. To this was added triethylamine (5 molar equivalents) in portions. The thick suspension was cooled to 6° C. and T3P (1.1 molar equivalents of a 1.57M in THF) was added drop-wise at 5-15° C. over 0.5 hr. The reaction mixture was allowed to warm to 22° C. and stirred at 22° C. for 2 hr. The mixture was diluted with water (6.5 volumes, 4° C. exotherm) and the mixture was stirred for 10 mins; the aqueous was separated and extracted with DCM (4.5 volumes). The combined organics were washed saturated aq sodium bicarbonate solution (5.5 volumes) and 20% brine solution (1.5 volumes). The organics were dried over anhydrous sodium sulphate, filtered and evaporated to give a brown oil. Yield: 96% of theoretical.

Provenance & Evidence