反应详情

13 g (20 mmol) of triphenylphosphine complex of nickel (II) chloride were added to a solution of 25.3 g (100 mmol) of 1-(4-nitrophenyl)cyclopentanoic acid in 200 ml of a 1:1 by volume mixture of methanol and tetrahydrofuran cooled in an ice bath. 10 g of sodium boronhydride were added to the cooled mixture in small portions over 10 minutes. The resulting mixture was then stirred at room temperature for 20 minutes, at the end of which time the reaction mixture was poured into 500 ml of water and the pH was then adjusted to 4 with concentrated hydrochloric acid. This caused the precipitation of crystals of 1-(4-aminophenyl)cyclopentanecarboxylic acid which were collected by filtration. 22.2 g (150 mmol) of potassium carbonate and 100 ml of tetrahydrofuran were then added to a suspension of the crystalline product in 100 ml of water which had been cooled in an ice bath, after which 9.0 ml (100 mmol) of methoxyacetyl chloride were added. After stirring the resulting mixture at the same temperature for 30 minutes, 200 ml of water were added, the mixture was washed with ether and the pH of the ether extract was then adjusted to 4 with concentrated hydrochloric acid. This mixture was allowed to stand at room temperature for 2 hours and the resulting crystals were collected by filtration to afford 25.4 g (yield 91.6%) of the desired compound as white crystals.

1. temperaturecooled in an ice bath
2. customthe precipitation of crystals of 1-(4-aminophenyl)cyclopentanecarboxylic acid which
3. filtrationwere collected by filtration
4. temperaturehad been cooled in an ice bath
5. stirringAfter stirring the resulting mixture at the same temperature for 30 minutes
6. washthe mixture was washed with ether
7. extractionthe pH of the ether extract
8. waitto stand at room temperature for 2 hours
9. filtrationthe resulting crystals were collected by filtration