Acetic Acid → HCID 68662630, compound

Participants

Reaction Steps

To a −78° C. solution of rac-(3aS,4S,7S,7aR)-tetrahydro-1H-4,7-methanoisoindole-1,3,5(4H)-trione (1.08 g, 6.03 mmol) (Kossakowski, Jerzy; Zawadowski, Teodor; Balicka, Eliza., Acta Poloniae Pharmaceutica (1997), 54(6), 479-481) in 50 ml of anhydrous THF was added methylmagnesium bromide (5.02 ml of a 3 M solution in THF, 15.07 mmol). After 2 hr, an additional 3 mL of methylmagnesium bromide solution was added. After another 2 hr, an additional 2 mL of methylmagnesium bromide solution was added. After 6 hr total at −78° C., the cooling bath was removed and the reaction allowed to warm to room temperature. The reaction was quenched with acetic acid (1.725 ml, 30.1 mmol) (Carefully). 200 uL of water was added, and the mixture was diluted with CH2Cl2 and 2 mL MeOH. The mixture was dried over Na2SO4, filtered, and concentrated to give a white foam. The foam was dissolved in 5% MeOH/CH2Cl2 and filtered through a plug of silica to give the titled compound as an off-white solid.

Provenance & Evidence