Reaktion #1807685

ord-ac3048f02d4b47059dcb80ddaf248134

Reaktionsgleichung

O=C(Cl)OC(Cl)(Cl)Cl
trichloromethyl chloroformate
COc1ccc(CN)cc1
4-methoxybenzylamine
COc1ccc(OCC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1
(2S)-1-[N-(t-butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2-(4-methoxyphenoxy) ethyl]pyrrolidine
C1COCCO1.Cl
hydrochloric acid 1,4-dioxane
COc1ccc(OCC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2)cc1.Cl
(2S)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]-l-(L-prolyl)pyrrolidine hydrochloride
→
COc1ccc(CNC(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(O)COc2ccc(OC)cc2)cc1
title compound
COc1ccc(CNC(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(O)COc2ccc(OC)cc2)cc1
(2S)-2-[1-Hydroxy-2-(4-methoxyphenoxy)ethyl]-l-[N-(4-methoxybenzylaminocarbonyl)-L-prolyl]pyrrolidine

Edukte

O=C(Cl)OC(Cl)(Cl)Cl
trichloromethyl chloroformate
COc1ccc(CN)cc1
4-methoxybenzylamine
COc1ccc(OCC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1
(2S)-1-[N-(t-butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2-(4-methoxyphenoxy) ethyl]pyrrolidine
C1COCCO1.Cl
hydrochloric acid 1,4-dioxane
COc1ccc(OCC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2)cc1.Cl
(2S)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]-l-(L-prolyl)pyrrolidine hydrochloride

Reagenzien

Keine

Lösungsmittel

CCN(CC)CC
triethylamine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeas obtained

Vorschrift

By the same procedure as in Example 24-A) using trichloromethyl chloroformate (0.20 ml), 4-methoxybenzylamine (449 mg), triethylamine (0.45 ml+0.89 ml) and (2S)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]-l-(L-prolyl)pyrrolidine hydrochloride (1.18 g) as obtained by treating (2S)-1-[N-(t-butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2-(4-methoxyphenoxy) ethyl]pyrrolidine obtained in Example 22-A) with 4N hydrochloric acid/1,4-dioxane, there was obtained 661 mg of the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05506256uspto-grants-1996_04