Sodium borohydride → HCID 178471787, compound

HRID 505298Notes

Reaction equation

HRID 505298 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]([CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH2:16]1)[C:6]1[C:7]([CH:12]=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:4]>CCO.O>[CH2:3]([N:5]([CH2:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][CH2:20]1)[C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178471786HCID 178471786, compound

Product 1

HCID 178471787HCID 178471787, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium borohydride (62.3 mg, 1.65 mmol) was added to a stirred solution of ethyl (trans-4-{[ethyl(2-formylpyridin-3-yl)amino]methyl}cyclohexyl)acetate (136.9 mg, 0.412 mmol) in EtOH (10 mL) at room temperature. The reaction was stirred at room temperature for 1 h, then diluted with water and most of the EtOH was removed in vacuo. The resulting aqueous slurry was extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo to afford ethyl [trans-4-({ethyl[2-(hydroxymethyl)pyridin-3-yl]amino}methyl)cyclohexyl]acetate. LCMS calc.=335.2; found=335.3 (M+1)+.

Workup

  1. customwas removed in vacuo
  2. extractionThe resulting aqueous slurry was extracted with EtOAc (3×20 mL)
  3. washthe combined extracts were washed with brine (5 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1147798b5241454c8c71794e552293a8
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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