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

HRID 712081Notes

Reaction equation

HRID 712081 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-53e3060670734247a0c6b9c7c0a33266
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…