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

HRID 712081노트

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HRID 712081 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-53e3060670734247a0c6b9c7c0a33266
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181271B2

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