1-(2,3-Dihydro-1,4-benzodioxin-5-yl)ethanone → 4-(Methoxycarbonyl)phenyl(3s,4s)-3-({[1-(2,3-dihydro-1,4-benzodioxin-5-yl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

HRID 732717

Reaktionsgleichung

Reaktionsgleichung von HRID 732717
[NH2:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)=[O:15])[CH2:4]1.[C:27]([C:30]1[C:39]2[O:38][CH2:37][CH2:36][O:35][C:34]=2[CH:33]=[CH:32][CH:31]=1)(=O)[CH3:28]>C1COCC1>[O:35]1[C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([CH:27]([NH:1][CH2:2][C@@H:3]3[C@@H:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:6][N:5]([C:14]([O:16][C:17]4[CH:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:22]=4)=[O:15])[CH2:4]3)[CH3:28])[C:39]=2[O:38][CH2:37][CH2:36]1

Komponenten

4

Edukt 2

HCID 212680521-(2,3-Dihydro-1,4-benzodioxin-5-yl)ethanoneHCID 68911676HCID 68911676, Verbindung

Produkt 1

HCID 689138824-(Methoxycarbonyl)phenyl(3s,4s)-3-({[1-(2,3-dihydro-1,4-benzodioxin-5-yl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylateAusbeute 39,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 2.0 ml THF solution of 253 mg of 4-(methoxycarbonyl)phenyl(3S,4S)-3-(aminomethyl)-4-phenylpyrrolidine-1-carboxylate and 144 mg of 5-acetylbenzodioxane was mixed with 0.12 ml of a boron trifluoride diethyl ether complex at 0° C. and stirred overnight at room temperature. The reaction solution was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel chromatography (chloroform-methanol) to obtain 146 mg of 4-(methoxycarbonyl)phenyl(3S,4S)-3-({[1-(2,3-dihydro-1,4-benzodioxin-5-yl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as a colorless amorphous substance. EP: 517.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. customthe thus obtained residue was purified by a silica gel chromatography (chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-a44eee1b2f0a4449b79e7922510b92ad
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585886B2

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