Sodium borohydride → HCID 66670254, compound

HRID 1514650Notes

Reaction equation

HRID 1514650 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=1[CH:25]=[O:26])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=1[CH2:25][OH:26])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86626939HCID 86626939, compound

Product 1

HCID 66670254HCID 66670254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 750 mg portion of ethyl 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-4-formyl-2-methyl-1H-pyrrole-3-carboxylate was suspended in 15 ml of ethanol, and 158 mg of sodium borohydride was added at 0° C., followed by stirring at room temperature for 2 hours. The solvent was evaporated under a reduced pressure, chloroform and water were added, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. By evaporating the solvent under a reduced pressure, 754 mg of ethyl 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-4-(hydroxymethyl)-2-methyl-1H-pyrrole-3-carboxylate was obtained as a colorless solid.

Workup

  1. customThe solvent was evaporated under a reduced pressure, chloroform and water
  2. additionwere added
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-0f893527366c4cc5b5a3167ff25c4499
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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