3-(Phenylsulfonyl)-6-Oxa-3-Azabicyclo[3.1.0]Hexane synthesis

Yield:955158-69-7 72%

Reaction Conditions:

Stage #1: 1-(benzenesulfonyl)-2,5-dihydro-1H-pyrrolewith 3-chloro-benzenecarboperoxoic acid in dichloromethane at 20; for 16 h;
Stage #2: with sodium hydrogencarbonate in dichloromethane;water;

Steps:

0-I

To a solution of 1-phenylsulfonyl-3-pyrroline (4.54 g, 21.69 mmol) in dichloromethane (100 ml), 3-chloroperoxybenzoic acid (10.7 g, 43.46 mmol) was added in portions. The suspension was stirred at r.t. for 16 h. Dichloromethane was added and the solution was washed with saturated solution of NaHCO₃, saturated solution of NaCl, dried over Na₂SO₄, filtered and concentrated. The crude was purified by flash chromatography: silica gel, gradient dichloromethane to dichloromethane:ethyl acetate (9:1), to give the product (3.52 g, 72%) as white solid. ¹H NMR (400 MHz, CDCl3): δ (ppm) 7.79 (m, 2H), 7.58 (m, 1H), 7.52 (m, 2H), 3.72 (d, J=12.7Hz, 1H), 3.58 (s, 2H), 3.38 (d, J1=12.7Hz, 2H).

References:

EP1849781,2007,A1 Location in patent:Page/Page column 91