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

HRID 1164646노트

반응식

HRID 1164646 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 12896954Dimethyl 2-methyl-4-(2-cyanophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate수율 72.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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% actic 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5a922993299f43099833b0a7603af4f7
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04370334

반응 노트

불러오는 중…