HCID 14547435, compound → HCID 70375348, compound

HRID 329690Notes

Reaction equation

HRID 329690 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](=[O:30])[CH2:24][C:25](OCC)=[O:26])=[C:10]1[C:31]([O:33][CH2:34][CH3:35])=[O:32].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[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:30])[CH2:24][CH2:25][OH:26])=[C:10]1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

4

Reactant 2

HCID 14547435HCID 14547435, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 70375348HCID 70375348, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}acetoacetate (0.99 g) (see European patent application publication no. 0132375) in tetrahydrofuran (10 ml) was added dropwise over five minutes to a stirred, ice-cooled suspension of lithium aluminium hydride (0.19 g) in tetrahydrofuran (20 ml). The ice-cooled mixture was stirred for 40 minutes, quenched into water and partitioned between ethyl acetate and 1M hydrochloric acid. The layers were separated and the organic layer was washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (8 g) using dichloromethane plus 0-50% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated and the residue triturated with ether/hexane. The resulting solid was collected, washed with ether and dried to give the title compound (0.25 g), m.p. 86°-89° C.

Workup

  1. temperaturecooled
  2. customquenched into water
  3. custompartitioned between ethyl acetate and 1M hydrochloric acid
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on SiO2 (8 g)
  9. customevaporated
  10. customthe residue triturated with ether/hexane
  11. customThe resulting solid was collected
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-9eef482b17174013a3b7ad4b4ce7b6da
Source dataset
uspto-grants-1990_01
Patent number
US04892881

Reaction notes

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