HCID 21973112, compound → 4-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane

HRID 11218

Reaction equation

[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][O:7][CH2:8][C:9]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][NH:12][C:11](=O)[CH2:10]1>C(OCC)C>[F:30][C:2]([F:1])([F:31])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][O:7][CH2:8][C:9]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 65 °C

Procedure

The mixture of Isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepan-2-one (90 mg, 0.20 mmol) in borone.THF complex solution (1.5 M in diethyl ether, 1.08 mL) was stirred at room temperature overnight and then at 65° C. for 1 hr. After cooling down, the mixture was concentrated under vacuum and methanol (0.4 mL) and 1N HCl solution (0.4 mL) was added and the mixture was stirred at 65° C. for 2 hr. After cooling down, the mixture was concentrated under vacuum and neutralized with 1N NaOH solution and extracted with dichloromethane 3 times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum to give the product as a clear colorless sticky oil (quantitative yield).

Workup

temperatureAfter cooling down
concentrationthe mixture was concentrated under vacuum and methanol (0.4 mL) and 1N HCl solution (0.4 mL)
additionwas added
temperatureAfter cooling down
concentrationthe mixture was concentrated under vacuum
extractionextracted with dichloromethane 3 times
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-f97e407b89e84fd9945ecbbef00955b6
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098203B2

Linked notes

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