Water → (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazin-3(4H)-one

HRID 1184618Notes

Reaction equation

HRID 1184618 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[CH:16]=[N:15][C:14]([CH:17]3[CH2:19][CH2:18]3)=[CH:13][N:12]=2)[CH2:7][N:6]1[CH2:20][C:21]([O:23]C)=O)=[N+]=[N-].O>CO.[Ni]>[CH:17]1([C:14]2[N:15]=[CH:16][C:11]([O:10][C@H:8]3[CH2:7][N:6]4[CH2:20][C:21](=[O:23])[NH:1][CH2:4][C@@H:5]4[CH2:9]3)=[N:12][CH:13]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 962WaterHCID 86680535methyl 2-((2S,4R)-2-(azidomethyl)-4-(5-cyclopropylpyrazin-2-yloxy)-pyrrolidin-1-yl)acetate

Product 1

HCID 86680536(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of the product from Example 201B (203 mg, 0.611 mmol) in methanol (20 mL) was added to Raney®-nickel 2800, water slurry (2030 mg, 34.6 mmol) in a 50 mL pressure bottle. The mixture was stirred at ambient temperature for 16 hours under hydrogen (30 psi). The mixture was filtered and concentrated in vacuo to give the title compound. MS (ESI) m/z 275 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f9aef4a48054734a7cc1fe8d28e0345
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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