Sodium Fluoride → tert-butyl(2S,4R)-2-[(dimethylamino)carbonyl]-4-fluoropyrrolidine-1-carboxylate

26.6 g of a mixture (approximately 3:1) of 1,1,2,3,3,3-hexafluoro-1-(diethylamino)propane and 1,2,3,3,3-pentafluoro-1-(diethylamino)-2-propene was added dropwise over a period of 10 minutes under ice cooling to a suspension of 25.7 g of the compound obtained in step 1-1a and 5.00 g of sodium fluoride in 260 mL of dichloromethane, after which the reaction mixture was stirred for 16 hours at room temperature. 100 mL of a 5% potassium carbonate aqueous solution was added under ice cooling to the reaction solution, and the reaction mixture was stirred for 30 minutes at the same temperature. After liquid separation, the aqueous layer thus obtained was extracted with chloroform, and the combined organic layer was washed with 50 mL of saturated brine and dried with magnesium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to column chromatography (silica gel 60, mobile phase: ethyl acetate/n-hexane=1/1 to 10/0; v/v) to obtain 12.2 g of the titled compound (pale yellow solid).

1. stirringthe reaction mixture was stirred for 30 minutes at the same temperature
2. customAfter liquid separation
3. customthe aqueous layer thus obtained
4. extractionwas extracted with chloroform
5. washthe combined organic layer was washed with 50 mL of saturated brine
6. dry with materialdried with magnesium sulfate
7. filtrationafter which the drying agent was filtered off
8. distillationthe solvent was distilled off under reduced pressure
9. customThe residue thus obtained

ORDレコード

ord-7a5cfd9f7de94b12a9f824563214f085

出典データセット

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07528124B2