(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide → (+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanecarboxamide

HRID 585712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585712
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]([C:21]([NH2:23])=[O:22])[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]([C:21]([NH2:23])=[O:22])[CH2:16]1

Komponenten

3

Edukt 1

HCID 22337819(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide

Produkt 1

HCID 22337782(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanecarboxamideAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide (22 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated to reflux 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 give the title compound as a white solid (5 mg, 31%). δH (CD3OD) 1.45-1.82 (6H, m), 2.07-2.19 (2H, m), 2.62-2.69 (1H, m), 3.00-3.09 (1H, m), 6.20-6.28 (2H, m), 6.89 (1H, d); m/z (ES+) 236 (M+H)+.

Aufarbeitung

  1. temperatureto reflux for 5 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

Quellen und Nachweise

ORD-Eintrag
ord-c23c7642d85b42419fd10dd3268f298d
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933319B2

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