Sodium borohydride → 4-(2-hydroxyethyl)-7-iodo-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one

HRID 711398Notes

Reaction equation

HRID 711398 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH2:7][CH:8]1[N:13]2[CH:14]=[C:15]([I:17])[CH:16]=[C:12]2[C:11](=[O:18])[NH:10][CH2:9]1)C>CCO>[OH:5][CH2:6][CH2:7][CH:8]1[N:13]2[CH:14]=[C:15]([I:17])[CH:16]=[C:12]2[C:11](=[O:18])[NH:10][CH2:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86658330HCID 86658330, compound

Product 1

HCID 867325494-(2-hydroxyethyl)-7-iodo-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.870 g, 23.0 mmol) was added to an ice-cooled stirred solution of ethyl(7-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate (1.00 g, 2.87 mmol) in EtOH (30 mL), under N2. The reaction mixture was stirred at room temperature for 18 h, and then it was quenched by water addition (10 ml). The solvent was evaporated to dryness and the residue dissolved in THF (30 ml)/brine (30 ml) and extracted with THF (3×30 mL). The organic phase was dried over Na2SO4 and concentrated to dryness to give the title compound (0.878 g, 2.87 mmol, 100%) as a solid.

Workup

  1. temperaturecooled
  2. customit was quenched by water addition (10 ml)
  3. customThe solvent was evaporated to dryness
  4. dissolutionthe residue dissolved in THF (30 ml)/brine (30 ml)
  5. extractionextracted with THF (3×30 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c3a0a1c6d4144b51a1518dfd15611a7e
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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