Sodium Hydroxide → (7S,8aS)-7-hydroxy-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861373Notes

Reaction equation

HRID 861373 reaction equation
C([O:9][C@@H:10]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=3)[CH2:17][C@@H:12]2[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[OH:9][C@@H:10]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=3)[CH2:17][C@@H:12]2[CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15886061(7S,8aS)-2-(5-Chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-7-yl benzoate

Product 1

HCID 15886073(7S,8aS)-7-hydroxy-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazineYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.52 g (1.45 mmol) of (7S,8aS)-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-7-yl benzoate (Example 17) in 50 mL of methanol was treated with 50 mL of 15% aqueous sodium hydroxide and stirred at ambient temperature for 30 min. The solvent was concentrated by half in vacuo and the residue extracted with chloroform (3×). The combined organic phase was dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 9:1 chloroform:methanol gave 0.25 g (68%) of the title compound. mp (base) 167°-168° C. m/z (MH+) 254.

Workup

  1. concentrationThe solvent was concentrated by half in vacuo
  2. extractionthe residue extracted with chloroform (3×)
  3. dry with materialThe combined organic phase was dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash silica gel chromatography with 9:1 chloroform

Sources & evidence

ORD record
ord-28a2cb057b584d8780d0215567ceef4c
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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