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

HRID 1461404

Reaktionsgleichung

Reaktionsgleichung von HRID 1461404
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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84716Hexadecyltributylphosphonium bromideKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2bb48a4ac5f44c5cb188937735ddc4c4
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075324

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