Carbon tetrabromide → HCID 86673576, compound

HRID 455279Notes

Reaction equation

HRID 455279 reaction equation
O[C@@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=3)[CH2:8][C@H:4]2[CH2:3]1.C(Br)(Br)(Br)[Br:24].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(#N)C>[Br:24][C@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=3)[CH2:8][C@H:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70976202HCID 70976202, compound

Product 1

HCID 86673576HCID 86673576, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (6S,7aR)-6-Hydroxy-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 33, step f) (900 mg, 2.848 mmol) in acetonitrile (10 ml) was added CBr4 (2.24 g, 8.544 mmol) at room temperature and stirred for 10 min. PPh3 (2.83 g, 8.544 mmol) was added and left stirring for 12 h at room temperature. The mixture was concentrated and the residue was purified through column chromatography over silica (elution with 10% ethyl acetate in hexane) to yield 850 mg (79%) of the title compound as white solid. LC-MS: 381.1 [M+1]+.

Workup

  1. waitleft
  2. stirringstirring for 12 h at room temperature
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified through column chromatography over silica (elution with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9c1783fe7ba847e89de5042afe5ef6ff
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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