HCID 9906491, compound → HCID 9861497, compound

HRID 366857Notes

Reaction equation

HRID 366857 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][CH2:16][CH2:17][C:18](OCC)=[O:19])[C:13]4[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:13]4[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 9906491HCID 9906491, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 9861497HCID 9861497, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 762 mg (2.45 mmol) of ethyl 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-butanoate, the title compound of Example 1, in 12 mL of THF was added 2.45 mL of LAH (1M in THF) at ambient temperature, and the resulting mixture was stirred overnight. The reaction was quenched with water, extracted with ether, and the combined extracts were dried, and concentrated in vacuo. The residue was purified by silica gel chromatography to give 538 mg (83%) of 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-butanol as a colorless glass: 1H NMR (CDCl3) δ 1.52 (quintet, J=7.8 Hz, 2H), 1.92 (quintet, J=7.7 Hz, 2H), 3.61 (t, J=6.2 Hz, 2H), 4.29 (t, J=7.7 Hz, 2H), 6.06 (s, 2H), 6.93 (d, J=8.4 Hz, 1H), 7.15-7.25 (m, 2H), 7.25-7.37 (m, 2H), 7.38-7.45 (m, 1H), 7.78-7.88 (m, 1H); HRMS (FAB) Calc'd for M+H: 311.1396, found: 311.1447. Anal. Calc'd for [C18H18N2O3 +0.09 CH2Cl2 ]: C, 68.39; H, 5.77; N, 8.82. Found: C, 68.39; H, 5.81; N, 8.82.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. customthe combined extracts were dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c391d22d69eb4b27bbb48c0344145d43
Source dataset
uspto-grants-2000_10
Patent number
US06130333

Reaction notes

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