1-Bromo-3-methylbutane → HCID 70976045, compound

HRID 455278Notes

Reaction equation

HRID 455278 reaction equation
[OH:1][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.[H-].[Na+].Br[CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29]>C1COCC1>[CH3:29][CH:28]([CH3:30])[CH2:27][CH2:26][O:1][C@@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]([F:20])([F:18])[F:19])=[CH:13][CH:14]=3)[CH2:8][C@H:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 70976202HCID 70976202, compound

Product 1

HCID 70976045HCID 70976045, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (100 mg, 0.316 mmol) in THF (3 mL) was added NaH (60% dispersion, 18.96 mg, 0.474 mmol) at room temperature and stirred for 30 min and then added 1-Bromo-3-methyl-butane (57.3 mg, 0.379 mmol) and left stirring for 12 h. The reaction mixture was quenched with NH4Cl aq., DCM was added. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified through column chromatography (elution with ethyl acetate in hexane) to afford 60 mg (49%) of the title compound. LC-MS: 386 [M+1]+.

Workup

  1. stirringstirring for 12 h
  2. customThe reaction mixture was quenched with NH4Cl aq., DCM
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified through column chromatography (elution with ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a7a47296c58a4495a9b874f49ba3cc68
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

Loading…