Hydrochloric Acid → methyl (1R,2R,4R,5S)-4-bromo-2-(2-bromophenyl)-5-hydroxycyclohexanecarboxylate

HRID 750786Notes

Reaction equation

HRID 750786 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C@H:5]1[C@@H:11]2[CH2:12][C@@H:8]([C:9](=[O:13])[O:10]2)[C@H:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Br:20])[CH2:6]1.Cl>CO>[Br:4][C@H:5]1[C@@H:11]([OH:10])[CH2:12][C@@H:8]([C:9]([O:2][CH3:1])=[O:13])[C@H:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Br:20])[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 11667632(1R,2R,4R,5S)-4-bromo-2-(2-bromophenyl)-6-oxabicyclo[3.2.1]octan-7-one

Product 1

HCID 11696819methyl (1R,2R,4R,5S)-4-bromo-2-(2-bromophenyl)-5-hydroxycyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared sodium methoxide (0.45 M in methanol) was added to a methanol (20 mL) solution of (1R,2R,4R,5S)-4-bromo-2-(2-bromophenyl)-6-oxabicyclo [3.2.1] octan-7-one (5.43 g, 15.1 mmol) with stirrng at rt for 1.5 hours. The mixture was then treated with 0.5 M HCl (50 ml) and the methanol was removed by rotary evaporation under reduced pressure. The residue was partitioned between water and ethyl acetate and the layers separated. The aqueous phase was extracted with additional ethyl acetate and the combined organics were washed with water, 5% Na2CO3 (2×75 mL) and brine, and dried (Na2SO4). Concentration in vacuo yielded methyl (1R,2R,4R,5S)-4-bromo-2-(2-bromophenyl)-5-hydroxycyclohexanecarboxylate as a faint-yellow solid after trituration with ether/hexanes.

Workup

  1. customthe methanol was removed by rotary evaporation under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with additional ethyl acetate
  5. washthe combined organics were washed with water, 5% Na2CO3 (2×75 mL) and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c346093196744dfd88608fd8e6aa9861
Source dataset
uspto-grants-2008_07
Patent number
US07405229B2

Reaction notes

Loading…