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

HRID 529710Notes

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-df90f4e9bc314b89aa166cbbd25fdac7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346825B2

Reaction notes

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