Acetic Acid → 1,2,3,4-Tetrahydro-1-methylquinoline

Participants

Reaction Steps

To a solution of tetrahydroquinoline (4.0 g, 30.0 mmol) in MeOH (60 mL) was added CH2O (37% aqueous solution, 2.7 mL, 36.3 mmol, 1.2 eq) and HOAc (1.73 mL, 30.0 mmol, 1.0 eq). The mixture was stirred at room temperature for 10 min then was cooled to 0° C. before NaBH3CN (1.98 g, 31.5 mmol, 1.05 eq) was added. After 1 h, the solvent was removed under reduced pressure. The reaction was quenched with saturated aqueous NaHCO3 then extracted with CH2Cl2 (5×30 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was used in the next step without further purification.

Provenance & Evidence