Hexamethyldisilazane → HCID 13370427, compound

Temperature

-78 °C

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).

1. stirringThe reaction mixture was stirred at -78° C. for 1 hr
2. temperatureto warm to 0° C. over about 30 min
3. stirringAfter stirring an additional 15 min at 0° C. the reaction
4. customwas quenched by addition of saturated aqueous ammonium chloride (5 ml)
5. additiondiluted with ether (50 ml)
6. washwashed with water (20 ml) and brine (10 ml)
7. dry with materialThe organic phase was dried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customto yield a yellow oil which
10. customwas chromatographed on a 1000μ silica gel plate (ether)

ORD record

ord-603552964252435c871d4dc1239e7688

Source dataset

uspto-grants-1985_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04491580