HCID 71544161, compound → HCID 86680453, compound

HRID 240446Notes

Reaction equation

HRID 240446 reaction equation
[CH2:1]=[C:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:32][N:14]3[CH2:15][CH2:16][N:17]([S:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)[CH3:3].[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:32][N:14]3[CH2:15][CH2:16][N:17]([S:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=4)(=[O:20])=[O:21])[CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 71544161HCID 71544161, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86680453HCID 86680453, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(7R,8aS)-7-{[5-(Prop-1-en-2-yl)pyrazin-2-yl]oxy}-2-{[4-(trifluoromethyl)phenyl]sulfonyl}octahydropyrrolo[1,2-a]pyrazine (240 mg, 0.512 mmol, Example 116) in ethanol (10 mL) was added to 20% palladium hydroxide on carbon (15 mg, 0.11 mmol). The mixture was stirred at room temperature for 16 hours under 30 psi of hydrogen. The mixture was filtered through a nylon membrane and concentrated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate=3:2) to give the title compound (217 mg, 90% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (s, 6H), 1.77 (m, 1H), 1.91 (m, 1H), 2.09 (m, 1H), 2.21-2.42 (m, 4H), 3.01 (m, 2H), 3.56 (m, 1H), 3.66 (m, 1H), 3.84 (m, 1H), 5.22 (m, 1H), 8.02 (m, 5H), 8.20 (m, 1H); MS (ESI) m/z 471 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (hexane/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-3c9ac1f943d04216ab66fbee21da5837
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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