Sodium Sulfate → (6,7-Dihydro-5H-cyclopenta[b]pyrazin-6-yl)methanol

HRID 2375336Notes

Reaction equation

HRID 2375336 reaction equation
C([O:3][C:4]([CH:6]1[CH2:14][C:9]2[N:10]=[CH:11][CH:12]=[N:13][C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)C>[N:10]1[C:9]2[CH2:14][CH:6]([CH2:4][OH:3])[CH2:7][C:8]=2[N:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 69311914ethyl 6,7-dihydro-5H-cyclopenta[b]pyrazine-6-carboxylate

Product 1

HCID 17859820(6,7-Dihydro-5H-cyclopenta[b]pyrazin-6-yl)methanolYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.5 g (23.4 mmol) of 6,7-dihydro-5H-cyclopentapyrazine-6 carboxylic acid ethyl ester (prepared by analogy to the method described in WO99/02517) in 90 ml of anhydrous tetrahydrofuran under argon was added 1.33 g (35.1 mmol) of lithium aluminum hydride. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with 100 ml of diethyl ether at 0° C. and treated with excess of a saturated aqueous solution of sodium sulfate. Further solid sodium sulfate was added and the organic phase was filtered to remove salts. The solvent was evaporated to dryness to give 3.3 g (94%) of product as an oil.

Workup

  1. filtrationthe organic phase was filtered
  2. customto remove salts
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-3413d2aaf7464c4b911b70bf374d0230
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

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