HCID 67230031, compound → HCID 67230182, compound

HRID 2067845Notes

Reaction equation

HRID 2067845 reaction equation
[NH2:1][C@H:2]1[CH2:6][C@:5]([C:11]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][N:16]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:12])([CH2:7][CH:8]([F:10])[F:9])[CH:4]=[CH:3]1.[H][H]>[Pd].CO>[NH2:1][C@@H:2]1[CH2:3][CH2:4][C@@:5]([C:11]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][N:16]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:12])([CH2:7][CH:8]([F:9])[F:10])[CH2:6]1

Participants

5

Reactant 2

HCID 67230031HCID 67230031, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67230182HCID 67230182, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl (1S,4S)-5-{[(1S,4S)-4-amino-1-(2,2-difluoroethyl)cyclopent-2-en-1-yl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (6.50 g, 17.5 mmol) and 5% palladium on carbon in methanol (100 ml) was stirred at room temperature under 46 psi of hydrogen for 21 hours. The reaction was filtered through celite and the filter cake washed with methanol. The filtrate and washings were concentrated under reduced pressure to give tert-butyl (1S,4S)-5-{[(1S,3R)-3-amino-1-(2,2-difluoroethyl)cyclopentyl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate as a brown oil (6.67 g, theoretical yield 6.54 g) which was used without further purification in the next step.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washthe filter cake washed with methanol
  3. concentrationThe filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee7fd490c97c450b90b4cb7e6e1d8216
Source dataset
uspto-grants-2012_10
Patent number
US08293903B2

Reaction notes

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