Hydrochloric Acid → (S)-3-(1-Carbamoyl-1,1-diphenylmethyl)-1-(7-oxohept-1-yl)pyrrolidine

Temperature

10 °C

To a three-necked 500 μL flask equipped with a mechanical stirrer, a nitrogen inlet, cooling bath, and a thermometer was added (S)-3-(1-carbamoyl-1,1-diphenylmethyl)-1-(7,7-dimethoxyhept-1-yl)pyrrolidine (16 g, 0.036 mol) and acetonitrile (100 mL). This mixture was cooled to about 10° C. and 100 mL of 1N aqueous hydrochloric acid was added while maintaining the reaction temperature at 20° C. or less. The resulting mixture was stirred at 20±5° C. for 2 hours. The reaction mixture was then extracted with dichloromethane (1×200 mL and 2×100 mL). The combined organic layers were washed with brine (200 mL) and dried with sodium sulfate (40 g). The organic layer was then concentrated under vacuum at about 25° C. to a volume of about 200 mL. This solution, containing the title intermediate as the hydrochloride salt, was used directly in the next step without further purification.

1. customTo a three-necked 500 μL flask equipped with a mechanical stirrer, a nitrogen inlet
2. temperaturecooling bath
3. temperaturewhile maintaining the reaction temperature at 20° C. or less
4. extractionThe reaction mixture was then extracted with dichloromethane (1×200 mL and 2×100 mL)
5. washThe combined organic layers were washed with brine (200 mL)
6. dry with materialdried with sodium sulfate (40 g)
7. concentrationThe organic layer was then concentrated under vacuum at about 25° C. to a volume of about 200 mL
8. additionThis solution, containing the title intermediate as the hydrochloride salt
9. customwas used directly in the next step without further purification

ORD record

ord-6f6228b7621e47c9a363a52bc3c79007

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285564B2