Sodium Carbonate → 7-Oxa-3-azabicyclo[4.1.0]heptan-3-yl(phenyl)methanone

Into a solution of 10 (2.27 g, 12.1 mmol) in CH2Cl2 (20 mL), a solution of 3-chloroperoxybenzoic acid (5.43 g, 77% pure, 24.3 mmol) in CH2Cl2 (40 mL) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 5 hrs. After the reaction was complete as determined by TLC (hexane/ethyl acetate, 1/1, v/v), saturated Na2CO3 solution (50 mL) was added into the reaction vial slowly with stirring. The reaction mixture was stirred for 30 min. The organic layer was washed with saturated Na2CO3 solution (50 mL×3), brine solution (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatograph using hexane/ethyl acetate (3/1, v/v) as the mobile phase to afford the product as a sticky oil (1.54 g, 62%). 1H NMR (CDCl3): δ 2.04-2.18 (m, 2H), 3.09-4.40 (m, 6H), 7.28-7.47 (m, 5H).

1. stirringwith stirring
2. stirringThe reaction mixture was stirred for 30 min
3. washThe organic layer was washed with saturated Na2CO3 solution (50 mL×3), brine solution (50 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by silica gel column chromatograph

ORD record

ord-840461a1af8d40d685e82eccafc25788

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658131B2