Carbon tetrabromide → HCID 86673575, compound

HRID 455266Notes

Reaction equation

HRID 455266 reaction equation
O[C@@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1.C(Br)(Br)(Br)[Br:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Br:23][C@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70976149HCID 70976149, compound

Product 1

HCID 86673575HCID 86673575, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of (6S,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 20, step a) (1.47 g, 4.36 mmol) and CBr4 (3.3 g, 8.72 mmol) in anhydrous THF (30 mL) was added PPh3 (2.3 g, 8.72 mmol) in THF (10 mL). Then the mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=10:1) to yield 1.50 g (84%) of the title compound as white solid. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 2H, J=9 Hz), 7.17 (d, 2H, J=9 Hz), 4.59-4.55 (m, 1H), 4.43-4.37 (m, 1H), 4.25-4.22 (m, 1H), 4.07 (t, 1H, J=9 Hz), 3.76 (dd, 1H, J1=3 Hz, J2=9 Hz), 3.62-3.56 (d, 1H, J=18 Hz), 2.43 (dd, 1H, J1=6 Hz J2=12 Hz), 1.99-1.92 (m, 1H). LC-MS: 365 [M+1]+.

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-bac7946a48934cec9cf197665b6fd8c2
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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