Sodium borohydride → HCID 67220195, compound

HRID 1258458Notes

Reaction equation

HRID 1258458 reaction equation
[OH:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[CH2:20][CH2:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH4-].[Na+]>C(O)C>[OH:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[CH2:20][CH2:21][CH:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67219754HCID 67219754, compound

Product 1

HCID 67220195HCID 67220195, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 7-hydroxy-1-(2-methoxyethyl)-2-methyl-6-(3-oxo-3-phenylpropyl)-1H-benzimidazole-5-carboxylate (2.08 g, 5.25 mmol, Step 9) in ethanol (50 mL) was added sodium borohydride (298 mg, 7.87 mmol) at room temperature. After stirring at the same temperature for 4 hours, the solvent was evaporated, and the residue was poured onto saturated sodium hydrogencarbonate aqueous solution, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20:1) to afford the title compound as a brown amorphous (2.08 g, 99%).

Workup

  1. customthe solvent was evaporated
  2. additionthe residue was poured onto saturated sodium hydrogencarbonate aqueous solution
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20:1)

Sources & evidence

ORD record
ord-3bdea470ddc649f2805cbde5cb782e81
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

Loading…