Acetic Acid → Dimethyl 2-methyl-4-(2-cyanophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1248737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248737
[CH3:1][C:2]1[NH:3][C:4]([CH:24]=[O:25])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]#[N:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[BH4-].[Na+].C(O)(=O)C>CO.O>[CH3:1][C:2]1[NH:3][C:4]([CH2:24][OH:25])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]#[N:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 15737326Dimethyl 2-methyl-4-(2-cyanophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate

Produkt 1

HCID 12896954Dimethyl 2-methyl-4-(2-cyanophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylateAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a cold solution of dimethyl 2-methyl-4-(2-cyanophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (2.3 g) in methanol (46 ml) at -5° C. was added portionwise sodium borohydride (140.7 mg) for 10 minutes, during which the temperature was kept at -4° to -5° C. with stirring. The mixture was stirred for additional 15 minutes at -6° C. The reaction mixture was diluted with water (20 ml) and acidified to about pH 5 with 50% acetic acid, and then condensed under reduced pressure to separate out crystalline product. After adding water (30 ml), the crystals were collected by filtration, washed thoroughly with water and dried. Thus obtained crystals (2.05 g) were recrystallized from methanol (15 ml) to give pure crystals of dimethyl 2-methyl-4-(2-cyanophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (1.67 g), mp 177° to 178° C.

Aufarbeitung

  1. customwas kept at -4° to -5° C.
  2. stirringThe mixture was stirred for additional 15 minutes at -6° C
  3. customcondensed under reduced pressure
  4. customto separate out crystalline product
  5. additionAfter adding water (30 ml)
  6. filtrationthe crystals were collected by filtration
  7. washwashed thoroughly with water
  8. customdried
  9. customThus obtained crystals (2.05 g) were recrystallized from methanol (15 ml)

Quellen und Nachweise

ORD-Eintrag
ord-84f512c495a24295b8178020d3953c1f
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04525478

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