Water → 2-(Pyridin-4-yl-amino)-butan-1-ol

HRID 433957Notes

Reaction equation

HRID 433957 reaction equation
C([O:3][C:4](=O)[CH:5]([N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[CH2:6][CH3:7])C.[BH4-].[Na+].O>C(O)C>[N:12]1[CH:13]=[CH:14][C:9]([NH:8][CH:5]([CH2:6][CH3:7])[CH2:4][OH:3])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12114317HCID 12114317, compound

Product 1

HCID 121143182-(Pyridin-4-yl-amino)-butan-1-olYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2-(tert-butoxycarbonyl-pyridin-4-yl-amino)butyric acid ethyl ester (0.33 g) in ethanol (5 ml) was treated with sodium borohydride (0.12 g) and the stirring was continued for 18 h. Water (1 ml) was added and the mixture was concentrated under reduced pressure. The residue was absorbed on to silica and the resulting powder was loaded on to a flash chromatography column which was eluted with methanol:chloroform:aqueous ammonia (10:89:1). The title compound (0.168 g) was obtained as an oil after evaporation of the product containing fractions.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was absorbed on to silica
  3. washwas eluted with methanol

Sources & evidence

ORD record
ord-315ff58f644d4de9b54f980c087c0b3a
Source dataset
uspto-grants-2003_12
Patent number
US06670381B2

Reaction notes

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