cis-5-[3,5-Bis(trifluoromethyl)phenyl]-4-ethenyl-1,3-oxazolidin-2-one → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-ethenyl-1,3-oxazolidin-2-one

HRID 529700Notes

Reaction equation

C(=O)(OCC)O[CH:3]([C:6]1[CH:11]=[C:10](F)[CH:9]=[CH:8][C:7]=1[Br:13])[CH:4]=[CH2:5].[F:18][C:19]([F:39])([F:38])[C:20]1[CH:21]=[C:22]([C@H:30]2[O:34][C:33](=[O:35])[NH:32][C@H:31]2[CH:36]=[CH2:37])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>C1C=C2C=CC3C(C=CC2=CC=1)=CC=CC=3.C(Cl)Cl>[F:39][C:19]([F:18])([F:38])[C:20]1[CH:21]=[C:22]([C@H:30]2[O:34][C:33](=[O:35])[N:32]([C@H:3]([C:6]3[CH:11]=[C:10]([C:19]([F:39])([F:38])[F:18])[CH:9]=[CH:8][C:7]=3[Br:13])[CH:4]=[CH2:5])[C@H:31]2[CH:36]=[CH2:37])[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1

Participants

Conditions

Temperature: 33 °C

Procedure

To a 500 mL RBF was added 1-(2-bromo-5-fluorophenyl)prop-2-en-1-yl ethyl carbonate (10.4 g, 29.5 mmol), (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-ethenyl-1,3-oxazolidin-2-one (4 g, 12.3 mmol), DCM (20 mL), and the Helmchen dibenzo[a,e]cyclooctatetraene (dbcot) iridium phosphoramidite catalyst complex (407 mg, 0.369 mmol) (Helmchen et al, Chem. Eur. J., 2010, 16, 6601-6615). The reaction was stirred at 33° C. for 2 days open to air. The reaction was filtered over Celite and purified by column chromatography to yield (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-ethenyl-1,3-oxazolidin-2-one (4.5 g, 7.65 mmol). 1H NMR (500 MHz, CDCl3) δ7.86 (m, 2H), 7.68 (s, 2H), 7.64 (s, 1H), 7.54 (d, J=6.5 Hz, 1H), 6.22 (m, 1H), 5.75 (m, 2H), 5.43 (m, 2H), 5.20 (m, 1H), 5.03 (d, J=5.0 Hz, 1H), 4.8 (d, J=8.5 Hz, 1H), 4.1 (m, 1H).

Workup

filtrationThe reaction was filtered over Celite
custompurified by column chromatography

Sources & evidence

ORD record: ord-00a9905135e2420c801e82cc0c8b59ae
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346825B2

Reaction notes

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