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

HRID 611063Notes

Reaction equation

HRID 611063 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[O:14][CH:15]=[CH:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.[C:17]([O:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>CO.C(O)(=O)C.ClCCl.[C].[Pd]>[C:28]([O:27][C:25]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][CH:15]=[CH:16][C:10]=2[CH2:9]1)=[O:26])([CH3:29])([CH3:30])[CH3:31].[C:25]([O:24][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26]

Participants

8

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 183773045-Benzyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine

Product 2

HCID 90495Di-tert-butyl dicarbonateHCID 196002415-Boc-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ad59f019346c48a0b0182aebd587ba74
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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