Benzyl Alcohol → HCID 57152973, compound

Temperature

60 °C

Benzyl alcohol (347 ml) was added to a suspension of sodium hydride (60% dispersion in oil, 89.6 g) in DMI (2.0 l), and the mixture was stirred at 60° C. for 1 hour. A solution of (S)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (478.4 g) obtained in Example 4-a), in DMI (150 ml) was dropwise added, and the mixture was stirred at said temperature for 2 hours. The reaction mixture was poured into a saturated aqueous solution of potassium hydrogensulfate and the mixture was extracted with toluene. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue (547.9 g) was dissolved in ethanol (3.0 l) and a 30% aqueous solution (1 l) of potassium hydroxide was added. The mixture was stirred at 76° C. for 3 hours. The reaction mixture was concentrated, acidified with 1.2N hydrochloric acid and washed with ethyl acetate. The aqueous layer was made basic with 10% sodium hydroxide and extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and concentrated to give the title compound (178.2 g).

1. stirringthe mixture was stirred
2. customfor 2 hours
3. extractionthe mixture was extracted with toluene
4. washThe organic layer was washed with water
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. dissolutionThe residue (547.9 g) was dissolved in ethanol (3.0 l)
8. additiona 30% aqueous solution (1 l) of potassium hydroxide was added
9. stirringThe mixture was stirred at 76° C. for 3 hours
10. concentrationThe reaction mixture was concentrated
11. washwashed with ethyl acetate
12. extractionextracted with methylene chloride
13. dry with materialThe extract was dried over anhydrous sodium sulfate
14. concentrationconcentrated

ORD record

ord-18090fb5863c485984c2573e15b1c0cf

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05536737