3-Benzyl 2-tert-butyl (1R,3S,4S,6R)-6-{[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]oxy}-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate → (1R,3S,4S,6R)-2-(tert-Butoxycarbonyl)-6-(3-ethoxy-3-oxopropoxy)-2-azabicyclo[2.2.1]heptane-3-carboxylic Acid

HRID 456766Notes

Reaction equation

HRID 456766 reaction equation
[CH2:1]([O:3][C:4](=[O:32])/[CH:5]=[CH:6]/[O:7][C@H:8]1[C@H:13]2[CH2:14][C@H:10]([C@@H:11]([C:22]([O:24]CC3C=CC=CC=3)=[O:23])[N:12]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9]1)[CH3:2].[H][H]>C(O)C.[Pd]>[C:18]([O:17][C:15]([N:12]1[C@H:11]([C:22]([OH:24])=[O:23])[C@H:10]2[CH2:14][C@@H:13]1[C@H:8]([O:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:32])[CH2:9]2)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 865989183-Benzyl 2-tert-butyl (1R,3S,4S,6R)-6-{[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]oxy}-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69133826(1R,3S,4S,6R)-2-(tert-Butoxycarbonyl)-6-(3-ethoxy-3-oxopropoxy)-2-azabicyclo[2.2.1]heptane-3-carboxylic AcidYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-benzyl 2-tert-butyl (1R,3S,4S,6R)-6-{[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]oxy}-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 30-2 (316 mg) in ethanol (8 mL), was added 10% palladium on carbon (60 mg). The mixture was stirred under 4 atm of hydrogen for 1 hr at room temperature. The resulting mixture was filtered through celite and washed with ethanol. The filtrate and washings were evaporated in vacuo and the residue was chromatographed on silica gel eluting with chloroform and methanol (19:1) to give the target compound (210 mg).

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. washwashed with ethanol
  3. customThe filtrate and washings were evaporated in vacuo
  4. customthe residue was chromatographed on silica gel eluting with chloroform and methanol (19:1)

Sources & evidence

ORD record
ord-83e8c5fa4b854c309efa775d11f5b149
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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