Tetrahydrofuran → (2S)-Cyclopentyl-(4-methylphenyl)acetic acid

HRID 618425Notes

Reaction equation

HRID 618425 reaction equation
C1COCC1.C(N(CC)CC)C.[CH2:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH:18]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:19]([OH:21])=[O:20]>O>[CH:14]1([C@@H:18]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[C:19]([OH:21])=[O:20])[CH2:15][CH2:16][CH2:17][CH2:13]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 189498872-Cyclopentyl-2-(p-tolyl)acetic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2.4 l of THF and 129.7 g (1.28 mol) of triethylamine are added, with stirring, to a suspension of 560 g (2.57 mol) of the compound from Example I in 4.8 l of water. The resulting solution is heated to 60° C., 155.4 g (1.28 mmol) of (S)-(-)-phenethylamine are added and the resulting suspension is stirred for 2 h at 60° C. The reaction mixture is cooled to 20° C., the precipitate is filtered off by suction, washed with 2.4 l of water/THF (2:1) and dried under reduced pressure.

Workup

  1. temperatureThe reaction mixture is cooled to 20° C.
  2. filtrationthe precipitate is filtered off by suction
  3. washwashed with 2.4 l of water/THF (2:1)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-337b9306ece6462ca98c42e9b260b275
Source dataset
uspto-grants-1999_09
Patent number
US05952498

Reaction notes

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