Hexamethyldisilazane → HCID 13370427, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (248)11 of 2.3M, 0.57 mmol) was added via syringe to a solution of hexamethyldisilazane (92 mg. 0.57 mmol) in freshly distilled tetrahydrofuran (3 ml) at -78° C. The resulting solution was stirred at -78° C. for 15 min prior to the addition of a solution of (S)-1-benzyloxycarbonylmethyl-4-benzene-sulfonyloxymethylazetidin-2-one (100 mg, 0.26 mmol) in tetrahydrofuran (1 ml). The reaction mixture was stirred at -78° C. for 1 hr., then was allowed to warm to 0° C. over about 30 min. After stirring an additional 15 min at 0° C. the reaction was quenched by addition of saturated aqueous ammonium chloride (5 ml), diluted with ether (50 ml) and washed with water (20 ml) and brine (10 ml). The organic phase was dried over magnesium sulfate and concentrated in vacuo to yield a yellow oil which was chromatographed on a 1000μ silica gel plate (ether) to yield 24.6 mg (41%) of (1R, 4S)-2-benzyloxycarbonylmethyl-2-azabicyclo[2.1,0]pentan-3-one. NMR (CHDl3) 7.33 (5H,S, aromatic), 5.15 (2H,S,CH2 --O), 3.8 (2H, ABq, CH2CO2 --), 3.9 (1H, ddd, J=1,3,4H1), 2.5 (1H, ddd, J=2,4,6.3, H4), 2.2 (1H, ddd, J=1,2,5,H5) 1.8 (1H, ddd, J=3,5,6,3,H5).

Provenance & Evidence