Potassium Carbonate → (S)-a-Hydroxy-cyclopentanepropanoic acid

HRID 2301167Notes

Reaction equation

HRID 2301167 reaction equation
C([O:4][C@@H:5]([CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[C:6]([OH:8])=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[OH:4][C@@H:5]([CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 540792742-(S)-acetoxy-3cyclopentyl propanoic acid

Product 1

HCID 21341064(S)-a-Hydroxy-cyclopentanepropanoic acidYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 395 mg (1.97 mmol) of 2-(S)-acetoxy-3-(cyclopentyl)propanoic acid (from Step E) in 10 mL MeOH and 1 mL of H2O was treated with 1.29 g (9.33 mmol) of K2CO3 and stirred at rt for 30 h. The volatiles were removed under reduced pressure. The crude product was partitioned between 100 mL of ether and 100 mL of H2O and the layers were separated. The aqueous layer was acidified to pH 1-2 using 2.0 N HCl and extracted with 3×150 mL of EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to give 287 mg (92%) of the title compound: 1H NMR (300 MHz) δ 1.11-2.15 (m, 11H), 4.27 (dd, J=8.1, 4.7, 1H), 6.5 (br, 1H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe crude product was partitioned between 100 mL of ether and 100 mL of H2O
  3. customthe layers were separated
  4. extractionextracted with 3×150 mL of EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6cad146b308c42bcb5785179d44ff26d
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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