Methanol → HCID 13175074, compound

Benzyl-(-)-pyroglutamide (60 g.) was suspended in one liter of tetrahydrofuran (THF) and stirred under nitrogen. The mixture was cooled to below 10° C. in an ice bath and one liter of 1 M BH3THF complex was slowly added. The mixture was stirred for 20 hours at room temperature and then refluxed for 28 hours. The reaction mixture was then cooled and 200 milliliters of methanol was added dropwise. The solvent was then removed and the residue dissolved in 2 N HCl and warmed in a steam bath for one hour. The solution was then cooled and filtered through Cellite®, basified with 50 percent NaOH, extracted with diethyl ether and the extract was washed with brine. The solution was dried and the solvent was removed to afford 2-benzylaminomethylpyrrolidine (64.2 g.) as a viscous oil.

1. temperatureThe mixture was cooled to below 10° C. in an ice bath
2. additionone liter of 1 M BH3THF complex was slowly added
3. stirringThe mixture was stirred for 20 hours at room temperature
4. temperaturerefluxed for 28 hours
5. temperatureThe reaction mixture was then cooled
6. customThe solvent was then removed
7. dissolutionthe residue dissolved in 2 N HCl
8. temperaturewarmed in a steam bath for one hour
9. temperatureThe solution was then cooled
10. filtrationfiltered through Cellite®
11. extractionextracted with diethyl ether
12. washthe extract was washed with brine
13. customThe solution was dried
14. customthe solvent was removed

ORD record

ord-6fa7ed70587f4c8e970e0dc06c513dc8

Source dataset

uspto-grants-1983_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04400511