Iodine → (+)-Sparteine

Participants

Reaction Conditions

Reaction Steps

To a solution of Lupanine (49.6 mg) in THF (3 mL) as ether was added NaBH4 (7.6 mg, 1.0 eq) and I2 (25.4 mg, 0.5 eq). The mixture was stirred at 80° C. for 16 hours and then cooled to room temperature. As alcohol MeOH (10 mL) was added and the mixture was subsequently poured into 50 mL of 5% aqueous alkaline hydroxide KOH. The resulting solution was extracted with Et2O (5×40 mL) as organic solvent, the organic extracts were dried over Na2SO4 and then concentrated to afford Sparteine as a colorless oil (41.2 mg, 88% yield).

Provenance & Evidence