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

HRID 720528Notes

Reaction equation

HRID 720528 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c437e4cc09984c4f80632e38488fc670
Source dataset
uspto-grants-2006_11
Patent number
US07135500B2

Reaction notes

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