Acetic Acid → HCID 54003879, compound

Sodium cyanoborohydride (17.4 mg, 0.27 mmol) was added portion-wise to a stirred solution of 2-phenethyl pyrrolidine (30 mg, 0.17 mmol) and 37% aqueous formaldehyde (0.07 mL, 0.87 mmol) in 1.5 mL acetonitrile at 25° C. The mixture was stirred for 15 min, acetic acid was added dropwise until the reaction was neutral, and the mixture was stirred for an additional 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in 10 mL diethyl ether and the ethereal solution was washed with 10 mL of saturated Na2CO3 and extracted twice with 5 mL of 1N HCl. The combined HCl solutions were then basicified with saturated Na2CO3 to obtain a pH=10 and extracted three times with 10 mL dichloromethane. The combined dichloromethane layers were washed with 10 mL of saturated NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified on thin layer chromatography to give 1-methyl-2-phenethyl pyrrolidine free base; 18 mg, 55% yield.

1. stirringthe mixture was stirred for an additional 2 hours
2. customThe solvent was removed under reduced pressure
3. dissolutionThe residue was dissolved in 10 mL diethyl ether
4. washthe ethereal solution was washed with 10 mL of saturated Na2CO3
5. extractionextracted twice with 5 mL of 1N HCl
6. customto obtain a pH=10
7. extractionextracted three times with 10 mL dichloromethane
8. washThe combined dichloromethane layers were washed with 10 mL of saturated NaCl
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified on thin layer chromatography

ORD record

ord-9e097fd3fdee497cb913c9a2091d2859

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168635B2