Ammonia → (3R)-1-benzylpyrrolidin-3-amine

Temperature

80 °C

In an autoclave were charged 5.303 g of (S)-1-benzyl-3-(methanesulfonyloxy)pyrrolidine (20 mmol, optical purity: 100% e.e.), and 42.53 g of 40% by weight aqueous ammonia (50 equivalent), which was heated to 80° C. whereby an internal pressure of 8 barr was observed. After allowing the reaction for 20 hrs, the reaction mixture was cooled to room temperature, followed by addition of 4.00 g of a 30% by weight aqueous sodium hydroxide solution (1.5 equivalent), and then ammonia was removed by distillation under reduced pressure. The residue was extracted with 30 mL of ethyl acetate three times, and the organic layers were combined. After washing with 3 mL of a saturated brine, drying over anhydrous magnesium sulfate, and concentration under reduced pressure gave 3.6146 g of a dark red oily material (reaction yield: 73%, optical purity: 92.4% e.e.).

1. customthe reaction for 20 hrs
2. temperaturethe reaction mixture was cooled to room temperature
3. customammonia was removed by distillation under reduced pressure
4. extractionThe residue was extracted with 30 mL of ethyl acetate three times
5. washAfter washing with 3 mL of a saturated brine
6. dry with materialdrying over anhydrous magnesium sulfate, and concentration under reduced pressure

ORD record

ord-6b24a42dd3ff40dba884c0c4a87c9856

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030501B2