Sodium borohydride → HCID 14810590, compound

HRID 1906770Notes

Reaction equation

HRID 1906770 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]([CH3:25])=[O:24])=[C:10]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH:23]([OH:24])[CH3:25])=[C:10]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19871309HCID 19871309, compound

Product 1

HCID 14810590HCID 14810590, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}acetone (0.46 g) and sodium borohydride (0.10 g) in ethanol (40 ml) was stirred at room temperature for 5 hours. The solution was evaporated, the residue dissolved in ethyl acetate and washed three times with water. The organic layer was dried over magnesium sulphate and evaporated. The residue was crystallized from diethyl ether/hexane to give the title compound (0.20 g), m.p. 110°-113°.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed three times with water
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. customevaporated
  6. customThe residue was crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-b33de2cedb8e406ab0c74fbc14d785b0
Source dataset
uspto-grants-1987_03
Patent number
US04654353

Reaction notes

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