rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester → HCID 58312626、化合物

HRID 527503

反応式

HRID 527503 の反応式
NC1C(C2C=CC(Cl)=C(Cl)C=2)CN(C(C2CCN(C(C3(C)CC3)=O)CC2)=O)C1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](=[O:68])[N:38]([C@H:41]2[C@H:45]([C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[C:48](Cl)[CH:47]=3)[CH2:44][N:43](C(C3CCN(C(C4(C)CC4)=O)CC3)=O)[CH2:42]2)[CH2:39][CH3:40])=[CH:32][CH:31]=1>>[F:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37](=[O:68])[N:38]([C@H:41]2[C@H:45]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)[CH2:44][NH:43][CH2:42]2)[CH2:39][CH3:40])=[CH:32][CH:31]=1

参加物

3

反応物 2

HCID 53247231rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl esterHCID 67238593HCID 67238593、化合物

生成物 1

HCID 58312626HCID 58312626、化合物

実験手順

In analogy to the procedure described for rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (example 1, f) the Boc protecting group was removed. The liberated amine was reacted to the respective carbamate in analogy to the procedure described for the synthesis of rac-{(3S,4R)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-ethyl-carbamic acid 4-fluoro-phenyl ester (example 1, h). The benzyl protecting group was removed in analogy to the procedure described for rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (example 1, d) to yield the title compound as amorphous crude brown foam. MS m/e: 363.3 [M+H]+.

後処理

  1. customwas removed
  2. customThe liberated amine was reacted to the respective carbamate in analogy to the procedure
  3. customThe benzyl protecting group was removed in analogy to the procedure

出典と根拠

ORDレコード
ord-83463d2b3d5f4d74a69cb085676ab295
出典データセット
uspto-grants-2016_05
特許番号
US09346786B2

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