Sodium borohydride → HCID 21905675, compound

HRID 1247426Notes

Reaction equation

HRID 1247426 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([CH:21]=[O:22])[C:15]=2[F:23])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([CH2:21][OH:22])[C:15]=2[F:23])[O:11][CH2:12][CH3:13])=[CH:25][CH:26]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21905731HCID 21905731, compound

Product 1

HCID 21905675HCID 21905675, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-formyl-phenyl)-2-ethoxy-acetamide (300 mg) in EtOH (1 ml) was treated with NaBH4 (66 mg) at 0°. The reaction mixture was stirred for 4 hrs at rt, then poured onto ice and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtrated and concentrated. The crude product was isolated by flash chromatography (CH2CH12=>CH2C2-12MeOH 4:1) to give (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-hydroxymethyl-phenyl)-2-ethoxy-acetamide (174 mg) as amourphous white solid. MS 361.3 ([M+H]+)

Workup

  1. additionpoured onto ice
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customThe crude product was isolated by flash chromatography (CH2CH12=>CH2C2-12MeOH 4:1)

Sources & evidence

ORD record
ord-c2e0a4102fe84b9cb4322864e55d8e16
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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