Tetrahydrofuran → HCID 17952496, compound

HRID 1828188Notes

Reaction equation

HRID 1828188 reaction equation
O1CCC[CH2:2]1.CO[C:8]([C:10]1[CH:23]=[CH:22][C:13]2[N:14]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[C:15](=[O:17])[NH:16][C:12]=2[CH:11]=1)=[O:9].[BH4-].[Li+]>CO>[CH:18]1([N:14]2[C:13]3[CH:22]=[CH:23][C:10]([CH2:8][OH:9])=[CH:11][C:12]=3[N:16]([CH3:2])[C:15]2=[O:17])[CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 695855151-cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 17952496HCID 17952496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a tetrahydrofuran (150 mL) solution of 1-Cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester 16.35 g, 62.8 mmol) was added lithium borohydride (63 mL, 2.0 M in tetrahydrofuran). The mixture was heated to 65° C. then methanol (2.5 mL) was added. The reaction was complete after 0.5 hours and was cooled and extracted into ethyl acetate from saturated ammonium chloride. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated to give 13.79 g of 1-Cyclobutyl-5-hydroxymethyl-3-methyl-1,3-dihydro-benzoimidazol-2-one.

Workup

  1. temperaturewas cooled
  2. extractionextracted into ethyl acetate from saturated ammonium chloride
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1e11e35ed78d47098fe3cd5bfe43a696
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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