1,2-Dichloroethane → HCID 86586084, compound

(1R*,2R*,5S*)-2-Amino-1-phenyl-8-azabicyclo[3.2.1]octane (Description 6; 97 mg, 0.48 mmol) and 3,5-bis(trifluoromethyl)benzaldehyde (121 mg, 0.5 mmol) were dissolved in 1,2-dichloroethane (10 mL) and treated with acetic acid (30 μL). The solution was stirred at room temperature for 16 hours then concentrated. The residue was taken up in methanol (10 mL) and treated with sodium cyanoborohydride (60 mg), then heated at 80° C. for 2 hours, concentrated in vacuo and the residue suspended in saturated sodium bicarbonate solution (10 mL). This was extracted with dichloromethane (2×10 mL) and the extracts dried (MgSO4), then concentrated. The residue was taken up in ethyl acetate (10 mL) and treated with ethereal hydrogen chloride (1M, 2 mL). The suspension formed was concentrated in vacuo and the solid remaining recrystallized from methanol/diethyl ether, to give the title compound as a white solid (167 mg, 0.33 mmol).

1. concentrationthen concentrated
2. additiontreated with sodium cyanoborohydride (60 mg)
3. temperatureheated at 80° C. for 2 hours
4. concentrationconcentrated in vacuo
5. extractionThis was extracted with dichloromethane (2×10 mL)
6. dry with materialthe extracts dried (MgSO4)
7. concentrationconcentrated
8. additiontreated with ethereal hydrogen chloride (1M, 2 mL)
9. customThe suspension formed
10. concentrationwas concentrated in vacuo
11. customthe solid remaining recrystallized from methanol/diethyl ether

ORD record

ord-7986b01e17f043b2a357ad1a872a5ecf

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555552B2