HCID 59769204, compound → (1S)-3-Oxo-1-(propan-2-yl)cyclopentane-1-carboxylic acid

Benzyl (1S)-1-isopropyl-3-oxocyclopentanecarboxylate (1.27 g, 4.88 mmol) was combined with Pd/C (10% Degussa, 500 mg) in 20 mL of methanol and stirred under a hydrogen atmosphere (balloon) for 2 h. The reaction had only proceeded part way (˜30% conversion) so the reaction mixture was filtered, another portion of Pd/C (500 mg) was added, and the mixture was stirred under a hydrogen atmosphere for 5 h. Since the reaction had now gone to completion, the reaction mixture was filtered through celite and concentrated to afford (1S)-1-isopropyl-3-oxocyclopentanecarboxylic acid that did not require further purification. Note that the large quantities of catalyst were used because the ester obtained after chiral separation must have been poisoned by an impurity. This was unique to this particular sample. Normally much smaller quantities of catalyst are used. 1H NMR was identical to that of the racemic acid above (Step D).

1. filtrationwas filtered
2. additionanother portion of Pd/C (500 mg) was added
3. stirringthe mixture was stirred under a hydrogen atmosphere for 5 h
4. filtrationthe reaction mixture was filtered through celite
5. concentrationconcentrated

ORD record

ord-6f9fd19d613c4061816528d55e4b7301

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700591B2