Ethyl Acetate → 4-{2-[1,1-Dimethyl-2-(2,4,6-trimethylphenyl)ethylamino]-1-hydroxyethyl}-3-methylbenzene-1,2-diol

HRID 720528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720528
C([O:8][C:9]1[C:10]([CH3:30])=[C:11]([C:23](=[O:29])[CH:24](OCC)O)[CH:12]=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.[CH3:31][C:32]([NH2:44])([CH3:43])[CH2:33][C:34]1[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=1[CH3:42].[BH4-].[Na+].C(OCC)(=O)C>C(O)C>[CH3:43][C:32]([NH:44][CH2:24][CH:23]([C:11]1[C:10]([CH3:30])=[C:9]([OH:8])[C:14]([OH:15])=[CH:13][CH:12]=1)[OH:29])([CH3:31])[CH2:33][C:34]1[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=1[CH3:42]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 218938531-(3,4-Bis-benzyloxy-2-methylphenyl)-2-ethoxy-2-hydroxyethanoneHCID 625487981-Mesityl-2-methylpropan-2-amine

Produkt 1

HCID 587409794-{2-[1,1-Dimethyl-2-(2,4,6-trimethylphenyl)ethylamino]-1-hydroxyethyl}-3-methylbenzene-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

350 mg (0.86 mmol) of 1-(3,4-bis-benzyloxy-2-methylphenyl)-2-ethoxy-2-hydroxyethanone and 198 mg (1.03 mmol) of 1,1-dimethyl-2-(2,4,6-trimethylphenyl)ethylamine were dissolved in 3 mL of ethanol and heated to 80° C. for 30 minutes in the presence of some molecular sieve. After cooling to ambient temperature, 33 mg (0.86 mmol) sodium borohydride was added and the mixture was stirred for 1 hour. The reaction mixture was combined with ethyl acetate and washed with sodium hydrogen carbonate solution. Then the organic phase was freed from solvent and chromatographed. In order to cleave the benzyl protecting groups, the ethanolamine-thus-obtained (364 mg) was dissolved in methanol, combined with 150 mg of Pearlman's catalyst, and hydrogenated at ambient temperature and under normal pressure. The reaction mixture was filtered through CELITE® filter agent and evaporated down. Chromatographic purification of the residue with dichloromethane and methanol as eluent yielded the target compound as a beige solid. Yield: 179 mg (29%); mass spectrometry: [M+H]+=391.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. washwashed with sodium hydrogen carbonate solution
  3. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-c437e4cc09984c4f80632e38488fc670
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135500B2

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