(+/-)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide → (+/-)-N-[3-(2,4-Dihydroxyphenyl)cyclohexyl]methanesulfonamide
Reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:16]1>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:16]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(±)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide (34 mg) was heated under reflux in methanol (2 ml) containing acidic ion exchange resin (0.3 g) for 5 hr. The reaction mixture was filtered and the resin was washed with methanol. The combined filtrate and washings were evaporated in vacuo and the crude residue was purified by preparative HPLC to furnish a mixture of diastereoisomers of the title compound as a pale pink solid (10 mg, 38%). δH (d4-MeOH) 1.20-2.00 (7H, overlapping m), 2.07 (1H, m), 2.90 (0.5H, m), 2.93 (1.5H, s), 2.97 (1.5H, s), 3.13 (0.5H, m), 3.30 (0.5H, m), 3.80(0.5H, m), 6.21-6.26 (1H, dd), 6.87 (0.5H, d), 6.89 (0.5H, d); m/z (ES−) 284 (M−H)−.