Formic Acid → HCID 59485010, compound

HRID 1850515Notes

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-909ef51a0e564d6588feec744d76a2e5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

Loading…