Cyproheptadine → 1-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol

HRID 382314

반응식

HRID 382314 반응식
CN1CCC(=C2C3C(=CC=CC=3)C=CC3C2=CC=CC=3)CC1.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]([C@H:33]([N:36]2[CH2:40][CH2:39][C@H:38]([O:41][CH2:42][O:43][CH3:44])[CH2:37]2)[CH2:34][OH:35])[CH:30]=[CH:31][CH:32]=1.[CH3:45][O:46][CH2:47][O:48][C:49]1[CH:50]=[C:51]([C@@H:55]([OH:66])[CH2:56][N:57]2[CH2:61][CH2:60][C@H:59]([O:62][CH2:63][O:64][CH3:65])[CH2:58]2)[CH:52]=[CH:53][CH:54]=1.[CH3:67][NH:68][C:69]1[CH:78]=[CH:77][C:72]([C:73]([O:75][CH3:76])=[O:74])=[CH:71][CH:70]=1>>[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]([C@H:33]([N:36]2[CH2:40][CH2:39][C@H:38]([O:41][CH2:42][O:43][CH3:44])[CH2:37]2)[CH2:34][OH:35])[CH:30]=[CH:31][CH:32]=1.[CH3:45][O:46][CH2:47][O:48][C:49]1[CH:50]=[C:51]([C@@H:55]([OH:66])[CH2:56][N:57]2[CH2:61][CH2:60][C@H:59]([O:62][CH2:63][O:64][CH3:65])[CH2:58]2)[CH:52]=[CH:53][CH:54]=1.[CH3:45][O:46][CH2:47][O:48][C:49]1[CH:50]=[C:51]([C@@H:55]([N:68]([C:69]2[CH:78]=[CH:77][C:72]([C:73]([O:75][CH3:76])=[O:74])=[CH:71][CH:70]=2)[CH3:67])[CH2:56][N:57]2[CH2:61][CH2:60][C@H:59]([O:62][CH2:63][O:64][CH3:65])[CH2:58]2)[CH:52]=[CH:53][CH:54]=1

참가 물질

7

반응물 4

HCID 2913CyproheptadineHCID 140375Methyl 4-methylaminobenzoateHCID 206405811-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanolHCID 206405882-(S)-(3-Methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol

생성물 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

실험 절차

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 reactin, the mixture of 2-(S)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol and 1-(R)-(3-methoxymethoxyphenyl)-2-(3-(S)-methoxymethoxypyrrolidin-1-yl)ethanol wth methyl 4-methylaminobenzoate in 54% yield according to the procedures similar to those described in Example 1 (i).

후처리

  1. customthose described in Preparation 3

출처 및 근거

ORD 기록
ord-51f013977164470cb7b97d2ae662dc99
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310061B2

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