Water → HCID 18752889, compound

HRID 1838068Notes

Reaction equation

HRID 1838068 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][C:5]([Cl:17])=[CH:4][N:3]=1.[BH4-].[Na+].O>C(O)C>[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[CH:6][C:5]([Cl:17])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86590075HCID 86590075, compound

Product 1

HCID 18752889HCID 18752889, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of t-butyl (E)-3-(2-amino-5-chloro-3-pyridinyl)-2-propenoate (500 mg, 2.0 mmol) in ethanol (10 ml) at RT was added sodium borohydride (317 mg, 8.4 mmol) portionwise and the mixture stirred for 16 h. After the addition of water, the ethanol removed in vacuo and the mixture extracted with diethyl ether. The ethereal extracts were dried over MgSO4, evaporated to dryness and purified by column chromatography upon silica gel using hexane-EtOAc (7:3) as eluant to give t-butyl 3-(2-amino-5-chloro-3-pyridinyl)propanoate as a colourless oil (340 mg, 1.3 mmol).

Workup

  1. customthe ethanol removed in vacuo
  2. extractionthe mixture extracted with diethyl ether
  3. dry with materialThe ethereal extracts were dried over MgSO4
  4. customevaporated to dryness
  5. custompurified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-10185af7e1274f4690ae22bc23c3dbfa
Source dataset
uspto-grants-2004_01
Patent number
US06673789B2

Reaction notes

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