Sodium borohydride → (2,6-Dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone

HRID 1392670Notes

Reaction equation

HRID 1392670 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[C:4]([Cl:17])[N:3]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:11])[CH:5]=[C:4]([Cl:17])[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 865939852,6-Dichloro-4-(pyrrolidine-1-carbonyl)-pyridine-3-carbaldehyde

Product 1

HCID 59678084(2,6-Dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the above aldehyde and sodium borohydride (400 mg, 10 mmol) in EtOH (50 mL) is stirred at room temperature for 1 hour. After evaporation of EtOH, EtOAc (40 mL) and water (40 mL) are added to the residue. The organic layer is separated, washed once with 1 N NaOH, 1N HCl and brine, dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (1:1 hexane:EtOAc) to give (2,6-dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone.

Workup

  1. customAfter evaporation of EtOH, EtOAc (40 mL) and water (40 mL)
  2. additionare added to the residue
  3. customThe organic layer is separated
  4. washwashed once with 1 N NaOH, 1N HCl and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-ea2e78f9821e4ed48f0d73071e11677c
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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