4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane → 4-(1-(5-Hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 1584437Notes

Reaction equation

HRID 1584437 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[N:21]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[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[N:21]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 184646564-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 184649364-(1-(5-Hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Alternatively, combine 4-(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (1.0 g, 2.7 mmol) and tetrahydrofuran (10 mL). Add a solution of lithium aluminum hydride in tetrahydrofuran (2.7 mL, 1 M, 2.7 mmol). After 18 hour, quench by slow portionwise addition of Glauber's salt (Na2SO4.10H2O) until gas evolution ceases. Add dichloromethane (20 mL) and celite and stir. Filter and evaporate in vacuo to give the title compound.

Workup

  1. customquench by slow portionwise addition of Glauber's salt (Na2SO4.10H2O) until gas evolution ceases
  2. filtrationFilter
  3. customevaporate in vacuo

Sources & evidence

ORD record
ord-fcbe30c5802d447ba347f1f2426d915a
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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