(+/-)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide → (+/-)-N-[3-(2,4-Dihydroxyphenyl)cyclohexyl]methanesulfonamide

HRID 585693Notes

Reaction equation

HRID 585693 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]1

Participants

3

Reactant 1

HCID 22337797(+/-)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide

Product 1

HCID 9795843(+/-)-N-[3-(2,4-Dihydroxyphenyl)cyclohexyl]methanesulfonamideYield 38.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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)−.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resin was washed with methanol
  3. customThe combined filtrate and washings were evaporated in vacuo
  4. customthe crude residue was purified by preparative HPLC
  5. customto furnish

Sources & evidence

ORD record
ord-719b8138519c42a5b68bae5e953811a1
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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