Borane → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

HRID 2290719Notes

Reaction equation

HRID 2290719 reaction equation
B.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=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)=[O:24])=[C:10]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>O1CCCC1>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=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][CH2:23][OH:24])=[C:10]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 6331BoraneHCID 13457220{[4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid

Product 1

HCID 703535674-(2-Chlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of borane in tetrahydrofuran (10 ml) was added dropwise over 10 minutes to a stirred, ice-cooled solution of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}acetic acid (2.0 g--see preparation 4 of European patent application publication No. 0100189) in tetrahydrofuran (20 ml) and the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 3 days, quenched with water (5 ml) and evaporated. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution and the organic layer was dried over MgSO4 and evaporated. The residual oil was purified by chromatography on silica gel (10 g) using hexane plus 20→50% dichloromethane followed by dichloromethane plus 0→1% methanol as eluant. Appropriate fractions were combined and evaporated and the resulting oil was crystallised from hexane to give the title compound (0.6 g), m.p. 125°-130°.

Workup

  1. custompreparation 4 of European patent application publication No
  2. customquenched with water (5 ml)
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialthe organic layer was dried over MgSO4
  6. customevaporated
  7. customThe residual oil was purified by chromatography on silica gel (10 g)
  8. customevaporated
  9. customthe resulting oil was crystallised from hexane

Sources & evidence

ORD record
ord-e3145acad1bc4764b5e6c291b2e6e5cd
Source dataset
uspto-grants-1986_10
Patent number
US04618609

Reaction notes

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