Methyl chloroformate → HCID 121006132, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tetrahydroquinolin-3-ol 10 (200 mg, 1.34 mmol) and methyl chloroformate (1 mL, 13 mmol) in CH2Cl2H2O (4:1), was added K2CO3 (1.8 g, 13 mmol) at 0° C. and the reaction mixture was further allowed to stir for 6 h at 25° C. Progress of reaction was monitored by TLC and after completion of reaction, a saturated solution of NH4Cl (20 mL) was added. The organic layer was separated; the aqueous layer was extracted with CH2Cl2 (2×50 mL). Combined organic layers were washed with brine (2×25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude products. Chromatographic purification of crude product with petroleum etherethyl acetate (6:4 v/v) as eluent gave 11 (291 mg) as oily liquid.

Provenance & Evidence