Sodium Thiosulfate → Ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-oxopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

To a suspension of Dess-Martin periodinane (0.233 g, 0.549 mmol) in CH2Cl2 (2.2 mL) at 0° C. was added a solution of (R)-ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.200 g, 0.499 mmol) in CH2Cl2 (1.5 mL). The resulting mixture was warmed to ambient temperature and stirred for 18 hours. The reaction mixture was cooled to 0° C. and quenched with saturated aqueous NaHCO3 (5 mL) containing Na2S2O3 (0.608 g, 3.85 mmol). The resulting mixture was warmed to ambient temperature and stirred for 10 minutes. The organic layer was separated, washed with saturated aqueous NaHCO3 (10 mL) followed by brine (10 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-oxopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.164 g, 82.4% yield). LC/MS (ES+APCI) m/z=399.1 (M+H).

1. temperatureThe reaction mixture was cooled to 0° C.
2. customquenched with saturated aqueous NaHCO3 (5 mL)
3. temperatureThe resulting mixture was warmed to ambient temperature
4. stirringstirred for 10 minutes
5. customThe organic layer was separated
6. washwashed with saturated aqueous NaHCO3 (10 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORDレコード

ord-96637b95acf244d184188ae2de2f3a9b

出典データセット

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08933084B2