Toluene → 2-(3-Phenyl-3-aminopropyl)-3-carboethoxy-5-carbomethoxy-6-methyl-4-(m-nitrophenyl)-1,4-dihydropyridine

HRID 1461404

반응식

HRID 1461404 반응식
C1(C)C=CC=CC=1.[BH4-].[Na+].[C:10]1([CH:16]([N:44]=[N+]=[N-])[CH2:17][CH2:18][C:19]2[NH:20][C:21]([CH3:43])=[C:22]([C:39]([O:41][CH3:42])=[O:40])[CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-:38])=[O:37])[CH:31]=3)[C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.O>[C:10]1([CH:16]([NH2:44])[CH2:17][CH2:18][C:19]2[NH:20][C:21]([CH3:43])=[C:22]([C:39]([O:41][CH3:42])=[O:40])[CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-:38])=[O:37])[CH:31]=3)[C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 1140TolueneHCID 4311764Sodium borohydrideHCID 199804232-(3-Phenyl-3-azidopropyl)-3-carboethoxy-5-carbomethoxy-6-methyl-4-(m-nitrophenyl)-1,4-dihydropyridine

생성물 1

HCID 199804762-(3-Phenyl-3-aminopropyl)-3-carboethoxy-5-carbomethoxy-6-methyl-4-(m-nitrophenyl)-1,4-dihydropyridine

시약·촉매·용매 2

HCID 84716Hexadecyltributylphosphonium bromide촉매HCID 962Water용매2회

반응 조건

온도
70 °C

실험 절차

120 ml of water are added to a toluene suspension (120 ml) of sodium borohydride (30 g), hexadecyl-tributylphosphonium bromide (2.27 g) and 15 g of the less polar diastereoisomer of 2-(3-phenyl-3-azidopropyl)-3-carboethoxy-5-carbomethoxy-6 -methyl-4-(m-nitrophenyl)-1,4-dihydropyridine. The mixture is stirred for 24 hours at 70° C., then cooled to room temperature, poured into water (200 ml), extracted with ethylacetate (200 ml), washed with water up to pH 7, dried and evaporated under vacuum. The crude oil (15 g) is purified by chromatography (silice 450 g eluent ethylacetate) to give 7.69 g of the less polar diastereoisomer of 2-(3-phenyl-3-aminopropyl)-3-carboethoxy-5-carbomethoxy-6-methyl-4-(m-nitrophenyl)-1,4-dihydropyridine as a glassy foam. It is dissolved in AcoEt (35 ml) and 1.87 g of maleic acid are added to give 8.2 g of the maleate salt C26H29O6N3 ·C4H4O4 (bright yellow crystal): p.f. 149-152° C.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethylacetate (200 ml)
  3. washwashed with water up to pH 7
  4. customdried
  5. customevaporated under vacuum
  6. customThe crude oil (15 g) is purified by chromatography (silice 450 g eluent ethylacetate)

출처 및 근거

ORD 기록
ord-2bb48a4ac5f44c5cb188937735ddc4c4
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075324

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