HCID 67229007, compound → HCID 67228776, compound

HRID 1844306Notes

Reaction equation

HRID 1844306 reaction equation
[NH2:1][C@H:2]1[CH2:6][C@:5]([C:9]([N:11]2[CH2:16][C@@H:15]3[CH2:17][C@H:12]2[CH2:13][N:14]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])([CH2:7][CH3:8])[CH:4]=[CH:3]1.[H][H]>[Pd].CO>[NH2:1][C@@H:2]1[CH2:3][CH2:4][C@@:5]([C:9]([N:11]2[CH2:16][C@@H:15]3[CH2:17][C@H:12]2[CH2:13][N:14]3[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[O:10])([CH2:7][CH3:8])[CH2:6]1

Participants

5

Reactant 2

HCID 67229007HCID 67229007, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67228776HCID 67228776, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl (1S,4S)-5-{[(1R,4S)-4-amino-1-ethylcyclopent-2-en-1-yl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.12 g, 6.32 mmol) and 5% palladium on carbon in methanol (35 ml) was stirred at room temperature under 48 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-ethylcyclopentyl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate as a brown oil/foam (2.46 g, theoretical yield 2.13 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-52db81939f6f486c86113437a838ae12
Source dataset
uspto-grants-2015_02
Patent number
US08946413B2

Reaction notes

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