Water → (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)acetonitrile

Temperature

50 °C

To a stirred solution of (S)-1-benzyl-3-(1-cyano-1,1-diphenylmethyl)pyrrolidine hydrochloride (8.55 g, 21.98 mmol) in methanol (44 mL) was added palladium on carbon (1.71 g) and ammonium formate (6.93 g, 109.9 mmol). The reaction mixture was heated to 50° C. with stirring for 3 h. The reaction was cooled to ambient temperature and water (20 mL) was added. The resulting mixture was filtered through a pad of Celite, washing with methanol (20 mL). The filtrate was collected and most of the methanol was removed in vacuo. The residue was mixed with isopropyl acetate (100 mL) and 10% aqueous sodium carbonate (50 mL). The resulting layers were separated and the aqueous layer was extracted with isopropyl acetate (50 mL). The organic layers were combined and dried over sodium sulfate (20 g). The sodium sulfate was filtered off and washed with isopropyl acetate (20 mL). The solvent was removed in vacuo to afford 5.75 g of the title intermediate as a light yellow oil (99.7% yield, 71% purity by HPLC).

1. temperatureThe reaction was cooled to ambient temperature
2. filtrationThe resulting mixture was filtered through a pad of Celite
3. washwashing with methanol (20 mL)
4. customThe filtrate was collected and most of the methanol
5. customwas removed in vacuo
6. additionThe residue was mixed with isopropyl acetate (100 mL) and 10% aqueous sodium carbonate (50 mL)
7. customThe resulting layers were separated
8. extractionthe aqueous layer was extracted with isopropyl acetate (50 mL)
9. dry with materialdried over sodium sulfate (20 g)
10. filtrationThe sodium sulfate was filtered off
11. washwashed with isopropyl acetate (20 mL)
12. customThe solvent was removed in vacuo

ORD record

ord-b11330312727482e9ff530ca03b66fb5

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07615566B2