Tetrahydrofuran → HCID 53667821, compound

Temperature

-50 °C

Butyl lithium (2.9 mL of 1M solution, 6 mmol) was added to a solution of N-isopropylcyclohexylamine (0.85 g, 6 mmol) in 10 mL of tetrahydrofuran at -20° C. After stirring for 30 minutes and further cooling to -50° C., N-ethylidenecyclohexanamine (3 mL of 2M solution, 6 mmol) was added. After stirring for an additional 30 minutes and continued cooling to -70° C., 2-cyclopropyl-3,3-bis(4-fluorophenyl)-2-propenal (0.85 g, 2 mmol) was added. The mixture was stirred for 4 hours at -70° C. and quenched with saturated ammonium chloride. The mixture was extracted with diethyl ether. The diethyl ether was dried with magnesium sulfate and concentrated in vacuo. The residue was stirred for 16 hours with a mixture of 50 mL of benzene, 15 mL of acetic acid and 35 mL of water. The mixture was diluted to 250 mL with water and extracted with diethyl ether. The extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 0.38 g of the title compound; m.p. =139°-140° C.

1. stirringAfter stirring for an additional 30 minutes
2. temperaturecontinued cooling to -70° C.
3. stirringThe mixture was stirred for 4 hours at -70° C.
4. customquenched with saturated ammonium chloride
5. extractionThe mixture was extracted with diethyl ether
6. dry with materialThe diethyl ether was dried with magnesium sulfate
7. concentrationconcentrated in vacuo
8. stirringThe residue was stirred for 16 hours with a mixture of 50 mL of benzene, 15 mL of acetic acid and 35 mL of water
9. additionThe mixture was diluted to 250 mL with water
10. extractionextracted with diethyl ether
11. washThe extracts were washed with saturated sodium bicarbonate solution
12. dry with materialdried over magnesium sulfate
13. concentrationconcentrated in vacuo
14. customThe residue was crystallized from hexane

ORD record

ord-681059652b284bd882becb90c2b332bc

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05011947