HCID 178500691, compound → HCID 178500650, compound

HRID 1713794Notes

Reaction equation

HRID 1713794 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=O)=O>CO.[Pd]>[C:10]1([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][CH2:18]2)[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 178500691HCID 178500691, compound

Product 1

HCID 178500650HCID 178500650, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (4520 mg) was added to a solution of methyl [trans-4-(4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)cyclohexyl]acetate (prepared as described in Patent Application WO2004/047755) (8100 mg) in MeOH (150 mL). The resulting suspension was stirred for 16 h under an atmosphere of Hydrogen. The suspension was filtered through diatomaceous earth and concentrated in vacuo to give a slurry. This was extracted into EtOAc (300 mL). The organic extract was washed with saturated aqueous sodium hydrogen carbonate solution (75 mL) and then brine (75 mL). The organic layer was dried and concentrated in vacuo to give the title compound (4720 mg) as an oil; 1H NMR δ 7.28-7.11 (5H, m), 3.58 (3H, s), 2.43 (1H+DMSO, m), 2.22 (2H, d), 1.83-1.67 (5H, m), 1.44 (2H, m), 1.13 (2H, m); MS m/e MH+ 233.

Workup

  1. filtrationThe suspension was filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. customto give a slurry
  4. extractionThis was extracted into EtOAc (300 mL)
  5. extractionThe organic extract
  6. washwas washed with saturated aqueous sodium hydrogen carbonate solution (75 mL)
  7. customThe organic layer was dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8396a0a9e497469b9817541a20f5e1be
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…