Hexane → Glycylbornane-10,2-sultam

Participants

Reaction Conditions

Reaction Steps

Over 20 minutes, 2 M trimethylaluminum in hexane (40 ml, 1.2 eq) was added to (2R)-bornane-10,2-sultam (15.7 g, 1.1 eq) in toluene (110 ml) at 0° C., then left for 30 minutes. Ethyl N-(diphenylmethylene)[1,2-13C2, 15N, 2,2-2H2]glycinate (18.1 g, 66.4 mmol) in toluene (10 ml) was added and the reaction stirred overnight. Heating to 50° C. for 3-4 hours drove the reaction to completion. Workup was effected by cooling the reaction in ice and carefully adding MeOD (20 ml). After 1 hour, D2O (30 ml) was carefully added. Filtering, extracting with ethyl acetate (2×250 ml), drying over MgSO4 and purifying by silica gel flash chromatography (Hexane: Ethyl Acetate 10:1 to 1:1) gave (2R)-N-(diphenylmethylene)[1,2-13C2, 15N, 2,2-2H2]glycylbornane-10,2-sultam (28.7 g, 99% yield) as an orange oil.

Provenance & Evidence