Methyl 4-methylaminobenzoate → 1-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol

HRID 381749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381749
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C@H:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][O:21][CH3:22])[CH2:15]2)[CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=1.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]([OH:44])[CH2:34][N:35]2[CH2:39][CH2:38][C@H:37]([O:40][CH2:41][O:42][CH3:43])[CH2:36]2)[CH:30]=[CH:31][CH:32]=1.[CH3:45][NH:46][C:47]1[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=1>>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C@H:11]([N:14]2[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][O:21][CH3:22])[CH2:15]2)[CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=1.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]([C@@H:33]([OH:44])[CH2:34][N:35]2[CH2:39][CH2:38][C@H:37]([O:40][CH2:41][O:42][CH3:43])[CH2:36]2)[CH:30]=[CH:31][CH:32]=1.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]([C@@H:33]([N:46]([C:47]2[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=2)[CH3:45])[CH2:34][N:35]2[CH2:39][CH2:38][C@H:37]([O:40][CH2:41][O:42][CH3:43])[CH2:36]2)[CH:30]=[CH:31][CH:32]=1

Komponenten

6

Edukt 3

HCID 140375Methyl 4-methylaminobenzoateHCID 206405882-(S)-(3-Methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanolHCID 70208489(3-Methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol

Produkt 3

HCID 206405811-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanolHCID 206405882-(S)-(3-Methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanolHCID 20640606Methyl 4-{N-[1-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)-ethyl]-N-methylamino}benzoate

Versuchsvorschrift

2-(S)-(3-Methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol and 1-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol were prepared from (R)-1-(3-methoxymethoxyphenyl)-1, 2-ethanediol-2-tosylate in 58% yield as a mixture according to the procedures similar to those described in Preparation 3. Title compound was prepared by reacting the mixture of 2-(S)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrroldin-1-yl)ethanol and (3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol with methyl 4-methylaminobenzoate in 54% yield according to the procedures similar to those described in Example 1 (i).

Aufarbeitung

  1. customthose described in Preparation 3

Quellen und Nachweise

ORD-Eintrag
ord-faa25c56889d41c582c3cb5abf95fdf8
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307061B2

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