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

HRID 1594598Notes

Reaction equation

HRID 1594598 reaction equation
C([O:9][C@@H:10]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[N:23]=[CH:22][C:21]([F: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[N:19]=[CH:20][C:21]([F:24])=[CH:22][N:23]=3)[CH2:17][C@@H:12]2[CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15886068(7S,8aS)-2-(5-Fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-7-yl benzoate

Product 1

HCID 15886075(7S,8aS)-7-Hydroxy-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazineYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.58 g (4.61 mmol) of (7S,8aS)-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-7-yl benzoate (Example 9) in 200 mL of methanol was treated with 50 mL of 15% aqueous sodium hydroxide. After 30 minutes, the solvent was removed and the residue partitioned between water and ethyl acetate. The layers were separated, the organic phase was dried (magnesium sulfate), filtered and evaporated to give 0.922 g (84%) of the title compound. 13C NMR (CDCl3): δ 39.4, 43.7, 49.0, 51.2, 62.2, 63.6, 69.9, 144.9, 145.2, 149.9, 153.2,158.9. m/z (MH+) 239.

Workup

  1. customthe solvent was removed
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4213cd5aac8041b3968e921779582faa
Source dataset
uspto-grants-2001_09
Patent number
US06284757B1

Reaction notes

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