1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86682277, compound

HRID 540452Notes

Reaction equation

[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C@@H:13]2[O:15][C@H:14]2[CH2:16][CH2:17][CH2:18][C@H:19]([NH:31]C(=O)OCC2C=CC=CC=2)[C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=2[Br:30])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[F:12][C:9]([F:11])([F:10])[C:7]1[CH:6]=[C:5]([C@H:13]([C@@H:14]2[CH2:16][CH2:17][CH2:18][C@@H:19]([C:20]3[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:21]=3[Br:30])[NH:31]2)[OH:15])[CH:4]=[C:3]([C:2]([F:42])([F:1])[F:43])[CH:8]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To benzyl {(1S)-4-{(2S,3S)-3-[3,5-bis(trifluoromethyl)phenyl]oxiran-2-yl}-1-[2-bromo-5-(trifluoromethyl)phenyl]butyl}carbamate (500 mg, 0.731 mmol) in DMF (2 mL) was added DBU (111 mg, 0.731 mmol). The system was heated to 125° C. for 6 hours. The solvent was removed in vacuo. The reaction was diluted with ethyl acetate and water. The organic was dried over sodium sulfate, filtered and concentrated. The resultant oil was purified by column chromatography to yield (R)-[3,5-bis(trifluoromethyl)phenyl]{(2S,6S)-6-[2-bromo-5-(trifluoromethyl)phenyl]piperidin-2-yl}methanol (280 mg, 0.509 mmol). 1H NMR (500 MHz, CDCl3) δ7.9 (s, 2H), 7.81 (d, J=5.4 Hz, 2H), 7.64 (d, J=8.3 Hz, 1H), 7.35 (d, J=8.3 Hz, 1H), 5.14 (d, J=8.2 Hz, 1H), 4.51 (m, 1H), 3.16 (m, 1H), 2.06 (m, 1H), 1.95 (m, 1H), 1.80 (m, 2H), 1.62 (m, 1H), 1.29 (m, 1H).

Workup

customThe solvent was removed in vacuo
additionThe reaction was diluted with ethyl acetate and water
dry with materialThe organic was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe resultant oil was purified by column chromatography

Sources & evidence

ORD record: ord-990ead0d3c224ff2a3bf6232f1792619
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871738B2

Reaction notes

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