methyl 7-[bis-(tert-butoxycarbonyl)amino]-4H-furo[2,3-c]-chromene-6-carboxylate → methyl cis-(3aRS,9bRS)-7-[bis-(tert-butoxycarbonyl)amino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate

HRID 927896Notes

Reaction equation

HRID 927896 reaction equation
[C:1]([O:5][C:6]([N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:9]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]2[C:12]([C:13]3[CH:25]=[CH:24][O:23][C:14]=3[CH2:15][O:16]2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCOCC1.C(O)(=O)C.[Pd]>[C:29]([O:28][C:26]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]2[C:12]([C@H:13]3[CH2:25][CH2:24][O:23][C@H:14]3[CH2:15][O:16]2)=[CH:11][CH:10]=1)=[O:27])([CH3:31])([CH3:32])[CH3:30]

Participants

6

Reactant 2

HCID 68093020methyl 7-[bis-(tert-butoxycarbonyl)amino]-4H-furo[2,3-c]-chromene-6-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86713278methyl cis-(3aRS,9bRS)-7-[bis-(tert-butoxycarbonyl)amino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylateYield 99.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 7-[bis-(tert-butoxycarbonyl)amino]-4H-furo[2,3-c]-chromene-6-carboxylate (Intermediate 3, 0.15 g) in a mixture of dioxane (15 mL) and acetic acid (1.5 mL) was treated under an atmosphere of nitrogen with palladium on carbon (10%, 0.02 g). The mixture was stirred and the nitrogen was replaced by hydrogen then the mixture was stirred under an atmosphere of hydrogen for 3 hours. The mixture was filtered through Celite, the pad was washed thoroughly with dioxane and the filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-7-[bis-(tert-butoxycarbonyl)amino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate (0.15 g) as a gum.

Workup

  1. stirringthe mixture was stirred under an atmosphere of hydrogen for 3 hours
  2. filtrationThe mixture was filtered through Celite
  3. washthe pad was washed thoroughly with dioxane
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-74f43402ee0243f4ac651fd1adca34ee
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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