1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl ester → tert-butyl N-[4-(3-fluorophenyl)-4-oxobutyl]carbamate

温度

-78 °C

In a round-bottomed flask was charged tert-butyl 2-oxopyrrolidine-1-carboxylate (2.2 g, 11.9 mmol) and THF (25 mL). The mixture was cooled down to −78° C. first, followed by slow addition of (3-fluorophenyl)magnesium bromide (17.8 mL, 17.8 mmol, 1.0 M solution in THF) over 15 minutes. The mixture was stirred for 3 hours, during which time the bath temperature rose from −78° C. to −10° C. The reaction was quenched by drop-wise addition of 1N HCl (2 mL) and warmed up to ambient temperature, followed by addition of EtOAc and water. After separating the organic layer, the aqueous layer was extracted with EtOAc three times. The combined organic layers was dried over Na2SO4 and concentrated to yield the product as a clear oil.

1. customrose from −78° C. to −10° C
2. customThe reaction was quenched by drop-wise addition of 1N HCl (2 mL)
3. temperaturewarmed up to ambient temperature
4. additionfollowed by addition of EtOAc and water
5. customAfter separating the organic layer
6. extractionthe aqueous layer was extracted with EtOAc three times
7. dry with materialThe combined organic layers was dried over Na2SO4
8. concentrationconcentrated

ORDレコード

ord-0e0d6802bbec4410b6ba92c729e66ce8

出典データセット

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09447104B2