Sodium borohydride → N-(5-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 1454836Notes

Reaction equation

HRID 1454836 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:13])([CH3:12])[CH3:14])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86233800N-(5-formyl-pyridin-2-yl)-2,2-dimethyl-propionamide

Product 1

HCID 24229196N-(5-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamideYield 48.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(5-formyl-pyridin-2-yl)-2,2-dimethyl-propionamide (6.96 g) under an argon atmosphere in MeOH (120 mL) was cooled to 0° C. and then treated portion wise with sodium borohydride (1.289 g). The cooling bath was removed, stirring was continued for 30 minutes and the reaction mixture was partitioned between half-saturated aqueous NH4Cl and AcOEt. The layers were separated, the organic layer dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (heptane/AcOEt 1:1 to 1:2) to give N-(5-hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (3.4 g) as a crystalline white solid. MS (ESI): 209.2 (MH+).

Workup

  1. customThe cooling bath was removed
  2. customthe reaction mixture was partitioned between half-saturated aqueous NH4Cl and AcOEt
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (heptane/AcOEt 1:1 to 1:2)

Sources & evidence

ORD record
ord-93532828e1874ba785d5a4da4fa70c5a
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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