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

HRID 1906767노트

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HRID 1906767 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-a593bed871ea42e4aa611f8185a9fb30
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04654353

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