Sodium Carbonate → (7S,8aS)-7-hydroxymethyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861348Notes

Reaction equation

HRID 861348 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:11][N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C@@H:5]2[CH2:4]1.Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC(C)C.C(OCC)(=O)C.O>[OH:1][CH2:2][C@@H:3]1[CH2:11][N:6]2[CH2:7][CH2:8][N:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][N:14]=3)[CH2:10][C@@H:5]2[CH2:4]1

Participants

7

Reactant 3

HCID 10340Sodium Carbonate2×HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 45099445HCID 45099445, compound

Product 1

HCID 22881891(7S,8aS)-7-hydroxymethyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31260Isoamyl AlcoholSolvent

Procedure

A solution of 1.0 g (6.4 mmol) of (7S,8aS)-7-hydroxymethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 13, Step A), 1.77 g (12.8 mmol) of 2-chloro-5-cyanopyridine and 2.71 g (25.6 mmol) of sodium carbonate in 50 mL of isoamyl alcohol was heated at reflux for 18 h. The mixture was cooled to room temperature, diluted with ethyl acetate and water, the pH was adjusted to 11 with sodium carbonate, the layers were separated, and the aqueous layer extracted with ethyl acetate. The combined organic phase was dried (magnesium sulfate), filtered and evaporated to give (7S,8aS)-7-hydroxymethyl-2-(5-cyanopyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine.

Workup

  1. temperatureat reflux for 18 h
  2. customthe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e29790a831124942bd78687e2255cd39
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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