HCID 71544158, compound → HCID 71544212, compound

HRID 240444Notes

Reaction equation

HRID 240444 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][N:17]3[CH2:20][C@H:21]([O:23][C:24]4[CH:29]=[N:28][C:27]([C:30]([CH3:32])=[CH2:31])=[CH:26][N:25]=4)[CH2:22][C@H:16]3[CH2:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Ni]>[C:1]([C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][N:17]3[CH2:20][C@H:21]([O:23][C:24]4[CH:29]=[N:28][C:27]([CH:30]([CH3:32])[CH3:31])=[CH:26][N:25]=4)[CH2:22][C@H:16]3[CH2:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 71544158HCID 71544158, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71544212HCID 71544212, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

(7R,8aS)-2-[(3-tert-Butylphenyl)sulfonyl]-7-{[5-(prop-1-en-2-yl)pyrazin-2-yl]oxy}octahydropyrrolo[1,2-a]pyrazine (164.3 mg, 0.360 mmol, Example 113) in ethanol (5 mL) was added to Raney® nickel 2800 water slurry (202.9 mg, 1.556 mmol) in a 20 mL pressure bottle. The mixture was stirred under 30 psi of hydrogen at ambient temperature for 15 hours. The mixture was filtered through a polypropylene membrane, the filtrate was concentrated, and the residue was purified by column chromatography on silica gel eluted with ethyl acetate/hexane (3:7) to give the title compound (56% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (m, 6H), 1.33 (s, 9H), 1.62 (m, 1H), 1.94 (m, 2H), 2.26 (m, 4H), 2.99 (m, 2H), 3.54 (m, 1H), 3.62 (m, 1H), 3.79 (m, 1H), 5.20 (m, 1H), 7.59 (m, 2H), 7.67 (m, 1H), 7.78 (s, 1H), 8.06 (m, 1H), 8.20 (m, 1H); MS (ESI) m/z 459 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a polypropylene membrane
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography on silica gel
  4. washeluted with ethyl acetate/hexane (3:7)

Sources & evidence

ORD record
ord-43c098ef60d14e4aaa0958988fa6dc9a
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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