Ethyl Acetate → HCID 57052302, compound

In an atmosphere of nitrogen, (2S,4R)-1-(3-pyridylmethyl)-2-methoxycarbonyl-4-methylsulfonyloxypyrrolidine (84.65 g) was dissolved in polyethylene glycol-400 (400 ml) followed by addition of lithium chloride (40 g, 0.943 mol). The mixture was warmed to 85°-90° C. and stirred at that temperature for 4-5 hours. The reaction mixture was then cooled to -20°~-25° C. and ethyl acetate (800 ml)-water (400 ml) was added thereto for extraction. After phase separation, the aqueous layer was adjusted to pH 9-9.5 with 24% sodium hydroxide in water (pH prior to adjustment: 4.8) and extracted with ethyl acetate (400 ml) twice. The ethyl acetate layer was combined and washed with a saturated aqueous sodium chloride solution (200 ml). The ethyl acetate solution was then concentrated to dryness under reduced pressure to provide (2S,4S)-1-(3-pyridylmethyl)-2-methoxycarbonyl-4-chloropyrrolidine (60.6 g) as an oil.

1. temperatureThe mixture was warmed to 85°-90° C.
2. temperatureThe reaction mixture was then cooled to -20°~-25° C.
3. extractionfor extraction
4. customAfter phase separation
5. extractionto adjustment: 4.8) and extracted with ethyl acetate (400 ml) twice
6. washwashed with a saturated aqueous sodium chloride solution (200 ml)
7. concentrationThe ethyl acetate solution was then concentrated to dryness under reduced pressure

ORD record

ord-d16f61be06e44b9293ac2161929ba7ec

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05675011