(+/-)-N-{3-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}acetamide → (+/-)-N-[3-(2,4-dihydroxyphenyl)cyclohexyl]acetamide

HRID 2307176Notes

Reaction equation

HRID 2307176 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][C:22](=[O:24])[CH3:23])[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][C:22](=[O:24])[CH3:23])[CH2:16]1

Participants

3

Reactant 1

HCID 22337801(+/-)-N-{3-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}acetamide

Product 1

HCID 22337784(+/-)-N-[3-(2,4-dihydroxyphenyl)cyclohexyl]acetamideYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-N-{3-[2,4-bis(methoxymethoxy)phenyl]cyclohexyl}acetamide (20 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated under reflux for 3 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 the title compound as a solid (5 mg, 34%). δH(CD3OD) 1.10-200 (1H, m), 2.90 (0.3H, tt), 3.08 (0.7H, tt), 3.70-380 (0.3H, m), 4.16 (0.7H, m), 6.20-6.26 (2H, m), 6.84-6.90 (1H, m); m/z (ES+) 250 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-1f4fbf62278d48a5806fc224acfaac87
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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