Diisopropylamine → HCID 12732756, compound

Temperature

45 °C

In an atmosphere of argon, to a solution of LDA (lithium diisopropylamide) prepared with a solution of diisopropylamine (60 ml) in anhydrous tetrahydrofuran (500 ml) and a 1.45M solution of butyl lithium in n-hexane (297 ml), a solution of cyclopentylacetic acid (25 g) in anhydrous toluene (100 ml) was dropped. The solution was stirred for 30 min. at room temperature and for 1 hr at 45° C. With blowing of air dried through phosphorus pentaoxide, the solution was stirred for 16 hrs. After reaction, the supernatant separated by decantation was diluted with water. The diluted solution was washed with diethyl ether, adjusted pH 2 with 6N hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then concentrated under reduced pressure. The residue was purified by recrystallization to give the title compound (17.1 g) having the following physical data:

1. dry with materialdried through phosphorus pentaoxide
2. stirringthe solution was stirred for 16 hrs
3. customAfter reaction
4. customthe supernatant separated by decantation
5. additionwas diluted with water
6. washThe diluted solution was washed with diethyl ether, adjusted pH 2 with 6N hydrochloric acid
7. extractionextracted with ethyl acetate
8. washThe extract was washed with a saturated aqueous solution of sodium chloride
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by recrystallization

ORD record

ord-cfaf2620a16b40ec8672e74077e1c66d

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04792550