Tetrahydrofuran → (1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

HRID 582070Notes

Reaction equation

C([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:8][CH:7]=1)=O)C.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[OH:3][CH2:4][C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Combine (1-(5-ethyoxycarbonylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine (2.7 mmol) and tetrahydrofuran (10 mL). Add a solution of lithium aluminum hydride (5.4 mL, 1.0M in tetrahydrofuran, 5.4 mmol). After 18 hours pour the reaction mixture into a beaker, dilute with dichloromethane, and cool to 0° C. With stirring add portionwise, Na2SO4.10 H2O until the evolution of gas ceases. Add dichloromethane to about double the volume, add celite, stir to form a thick slurry, and filter. Evaporate the filtrate in vacuo to give (1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine.

Workup

additionAfter 18 hours pour the reaction mixture into a beaker
additionadd portionwise
stirringstir
customto form a thick slurry
filtrationfilter
customEvaporate the filtrate in vacuo

Sources & evidence

ORD record: ord-0ea9a82700484a76b7d31af96d497e53
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922737

Reaction notes

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