Di-tert-butyl dicarbonate → Di-tert-butyl dicarbonate

To a solution of 15.023 g (70.438 mmol) of 5-benzyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 100 ml of methanol, 2 ml of acetic acid was added, followed by hydrogenation over 5 g of 10% palladium-carbon (50% hydrated) at room temperature at atmospheric pressure for 8 hours. The mixture was filtered using Celite to remove the catalyst; the Celite was washed with methanol 3 times. The combined methanol solution was evaporated under reduced pressure. The resulting residue (crude 4,5,6,7-tetrahydrofuro[3,2-c]pyridine) was dissolved in 100 ml of dichloromethane. To this solution, a solution of 15.4 g (70.4 mmol) of di-tert-butyl dicarbonate in 50 ml of dichloromethane was added dropwise at room temperature, followed by stirring for 0.5 hours. The solvent was distilled off under reduced pressure; the resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to yield 5-tert-butoxycarbonyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine as a mixture with di-tert-butyl dicarbonate.

1. filtrationThe mixture was filtered
2. customto remove the catalyst
3. washthe Celite was washed with methanol 3 times
4. customThe combined methanol solution was evaporated under reduced pressure
5. dissolutionThe resulting residue (crude 4,5,6,7-tetrahydrofuro[3,2-c]pyridine) was dissolved in 100 ml of dichloromethane
6. distillationThe solvent was distilled off under reduced pressure
7. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

ORD-Eintrag

ord-ad59f019346c48a0b0182aebd587ba74

Quelldatensatz

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05998433