Lithium aluminum hydride → {(1R,3S)-3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}methanol

HRID 712081ノート

反応式

HRID 712081 の反応式
[AlH4-].[Li+].[N+:3]([C:6]1[C:7]([NH:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([C:21](OCC)=[O:22])[CH2:17]2)=[C:8]2[S:14][CH:13]=[CH:12][C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4]>O1CCCC1>[N+:3]([C:6]1[C:7]([NH:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([CH2:21][OH:22])[CH2:17]2)=[C:8]2[S:14][CH:13]=[CH:12][C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4]

参加物

4

反応物 2

HCID 28112Lithium aluminum hydrideHCID 86717535ethyl (1R,3S)-3-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentanecarboxylate

生成物 1

HCID 86717537{(1R,3S)-3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}methanol収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Lithium tetrahydroaluminate (20.4 mg, 0.537 mmol) was added to a solution of ethyl (1R,3S)-3-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentanecarboxylate (0.15 g, 0.45 mmol) in tetrahydrofuran (4.0 mL) with stirring at about 0° C. The resulting mixture was kept cold and stirred for 40 min. Fieser workup was performed followed by filtration through Celite and concentrated. The crude was purified using silica gel, eluted with 40-100% EtOAc in hexanes to give 70 mg (50%) of the desired product. LCMS calculated for C13H16N3O3S (M+H)+: m/z=294.1. Found: 294.0.

後処理

  1. stirringstirred for 40 min
  2. filtrationFieser workup was performed followed by filtration through Celite
  3. concentrationconcentrated
  4. customThe crude was purified
  5. washeluted with 40-100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-53e3060670734247a0c6b9c7c0a33266
出典データセット
uspto-grants-2015_11
特許番号
US09181271B2

反応ノート

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