Carbon tetrabromide → (6S,7aS)-6-Bromo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

HRID 455255Notes

Reaction equation

HRID 455255 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@H:21]1[CH2:40][N:24]2[C:25](=[O:39])[N:26]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)[CH2:27][C@@H:23]2[CH2:22]1.C(Br)(Br)(Br)[Br:42]>C1COCC1>[Br:42][C@@H:21]1[CH2:40][N:24]2[C:25](=[O:39])[N:26]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)[CH2:27][C@@H:23]2[CH2:22]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70976331(6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

Product 1

HCID 86673574(6S,7aS)-6-Bromo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.7 g, 6.5 mmol) was added to a solution of (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (1.0 g, 3.3 mmol) and CBr4 (2.2 g, 6.6 mmol) in anhydrous THF (50 mL), the mixture was stirred at room temperature for 30 minutes under N2 protection. Then the mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=3:1) to give 1.15 g (95%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.61 (d, 2H, J=9.3 Hz), 7.21 (d, 2H, J=8.4 Hz), 4.48-4.42 (m, 1H), 4.19 (dd, 1H, J1=13.2 Hz, J2=2.7 Hz), 4.11-4.02 (m, 2H), 3.92-3.88 (m, 1H), 3.53 (dd, 1H, J1=13.5 Hz, J2=5.4 Hz), 2.81-2.71 (m, 1H), 2.26-2.18 (m, 1H). LC-MS: 365.0 [M+1]+.

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3d9086bb908f44a58a91c47f57edd994
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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