Sodium borohydride → HCID 14810590, compound

HRID 2290721Notes

Reaction equation

HRID 2290721 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 and the residue was dissolved in ethyl acetate and washed three times with water. The organic layer was dried over MgSO4 and evaporated. The residue was crystallised 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 was dissolved in ethyl acetate
  3. washwashed three times with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. customThe residue was crystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-f0175aca5be448a29b105ddf85d12eaa
Source dataset
uspto-grants-1986_10
Patent number
US04618609

Reaction notes

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