Triethylamine → HCID 19735100, compound

Participants

Reaction Steps

Ethyl chlorocarbonate(80 mg) was added to a solution of Compound 113 (200 mg) and triethylamine (0.10 ml) in anhydrous tetrahydrofuran (1 ml) at -15° C. under an argon atmosphere and the mixture was stirred at -15° to -10° C. for 30 minutes. The resulting precipitate was filtered off and the filtrate was added to a solution of sodium borohydride (67 mg) in water (0.7 ml) at 10° C. After completion of the addition, the mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was extracted by addition of water and ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography to obtain 6-hydroxymethyl-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (110 mg) (Compound 115). Likewise, Compound 145 was prepared from Compound 114.

Provenance & Evidence