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

8.85 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 2 minutes under ice cooling to a suspension of 8.54 g of the compound obtained in step 1-1b and 1.67 g of sodium fluoride in 90 mL of dichloromethane, after which the reaction mixture was stirred for 15 hours at room temperature. 200 mL of a saturated sodium hydrogencarbonate aqueous solution was added dropwise to the reaction solution over a period of 3 minutes, and the reaction mixture was stirred for 1 hour. After liquid separation, the aqueous layer was extracted with chloroform (30 mL×2), 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 reaction mixture was concentrated 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 7.54 g of the titled compound (pale yellow solid).

1. stirringthe reaction mixture was stirred for 1 hour
2. customAfter liquid separation
3. extractionthe aqueous layer was extracted with chloroform (30 mL×2)
4. washthe combined organic layer was washed with 50 mL of saturated brine
5. dry with materialdried with magnesium sulfate
6. filtrationafter which the drying agent was filtered off
7. concentrationthe reaction mixture was concentrated under reduced pressure
8. customThe residue thus obtained

ORD-Eintrag

ord-4b4ebc80d4454c65a2ab4a904986eab6

Quelldatensatz

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07528124B2