(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl(2S)-cyclopentyl(4-methylphenyl)ethanoate → (2S)-Cyclopentyl-(4-methylphenyl)acetic acid

HRID 877192Notes

Reaction equation

HRID 877192 reaction equation
[CH:1]1([C@@H:6]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:7]([O:9][C@@H]2C[C@H](C)CC[C@H]2C(C)C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[CH:1]1([C@@H:6]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 58136656(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl(2S)-cyclopentyl(4-methylphenyl)ethanoate

Product 1

HCID 28293121(2S)-Cyclopentyl-(4-methylphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

50.0 g (0.140 mol) of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl(2S)-cyclopentyl(4-methylphenyl)ethanoate were stirred under reflux for 16 h in 500 ml of trifluoroacetic acid. The trifluoroacetic acid was then removed on a rotary evaporator and the residue was taken up in 500 ml each of water and ethyl acetate. After extraction, the organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue was taken up in 1.5 liters of water, adjusted to pH 10 with aqueous sodium hydroxide solution and washed twice with in each case 300 ml of tert-butyl methyl ether. The aqueous phase was then adjusted to pH 4 using concentrated hydrochloric acid and extracted twice with in each case 300 ml of ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator. This gave 27.4 g (89% of theory) of the title compound.

Workup

  1. customThe trifluoroacetic acid was then removed on a rotary evaporator
  2. extractionAfter extraction
  3. washthe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. washwashed twice with in each case 300 ml of tert-butyl methyl ether
  7. extractionextracted twice with in each case 300 ml of ethyl acetate
  8. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-16c652c82ba24634a0363ca071b37075
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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