(R)-2-Amino-5-(3-pyridyl)pentane → (S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide

HRID 2232158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232158
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[C@@H:14]2[CH2:16][C:15]2([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=CC=1)([O-])=O.[CH3:34][C@@H:35]([NH2:45])[CH2:36][CH2:37][CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1>O1CCCC1>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([C:15]2([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:16][C@@H:14]2/[CH:13]=[CH:12]/[C:11]([NH:45][C@@H:35]([CH3:34])[CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[O:10])[CH:30]=[CH:29][CH:28]=1

Komponenten

4

Edukt 2

HCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 70374114(S)-(E)-3-[2,2-bis(3-methoxyphenyl)cyclopropyl]-2-propenoic acid 4-nitrophenyl ester

Produkt 1

HCID 86742538(S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamideAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

As in example 141, (S)-(E)-3-[2,2-bis(3-methoxyphenyl)cyclopropyl]-2-propenoic acid 4-nitrophenyl ester (2.2 g) was reacted with (R)-alpha-methyl-3-pyridinebutanamine (0.81 g) in tetrahydrofuran (15 mL) at ambient temperature overnight. The crude product, isolated in the usual manner, was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to give 1.4 g of (S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide, mp 104°-106° C.

Aufarbeitung

  1. customThe crude product, isolated in the usual manner
  2. customwas purified by HPLC (ethyl acetate)
  3. customcrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-52d96faf0f194649b89f0c28c0c36a3c
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04786646

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