Formic Acid → HCID 59485010, compound

HRID 2063921Notes

Reaction equation

C(O)C.C(O[CH2:12][C:13]1([CH3:39])[CH2:17][C:16]2[C:18]([CH3:38])=[C:19]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1)C1C=CC=CC=1.[CH:40]([OH:42])=[O:41]>[C].[Pd]>[CH:40]([O:42][CH2:12][C:13]1([CH3:39])[CH2:17][C:16]2[C:18]([CH3:38])=[C:19]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)[CH2:26][CH2:25]3)[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1)=[O:41]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethanol (7.0 mL) containing 1-{2-[(benzyloxy)methyl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-5-yl}-4-(4-methoxyphenyl)piperazine (30 mg, 0.0628 mmol) synthesized in Example 134, 10% palladium carbon (500 mg) and formic acid (7.0 mL) were serially added, and the mixture was stirred at 100° C. for 15 hours. After cooled to room temperature, palladium carbon was removed by filtration, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 97:3-80:20) and crystallized from ethyl acetate-hexane to obtain 290 mg of the title compound (yield: 49%). Melting point was 120 to 124° C.

Workup

additionwere serially added
temperatureAfter cooled to room temperature
custompalladium carbon was removed by filtration
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 97:3-80:20)
customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-0fb84a30801b41c2a72766ef97c85c93
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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