Sodium Bicarbonate → HCID 178489522, compound

HRID 1712562Notes

Reaction equation

HRID 1712562 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][CH:39]=[CH:38][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][C:25]2[C:30]3[NH:31][C:32]([C:34](OC)=[O:35])=[N:33][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[CH:13][CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:41]=[CH:40][CH:39]=[CH:38][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][C:25]2[C:30]3[NH:31][C:32]([CH2:34][OH:35])=[N:33][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 178499036HCID 178499036, compound

Product 1

HCID 178489522HCID 178489522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.100 g of methyl 7-(4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1H-benzoimidazole-2-carboxylate (Example 247) and 5.0 ml of tetrahydrofuran is cooled to 0° C. and admixed with 0.028 g of lithium aluminium hydride. The mixture is kept at room temperature over 2 hours. The reaction mixture is poured onto 1M sodium hydrogencarbonate solution and extracted with ethyl acetate (2×25 ml). The organic phases are washed with brine (20 ml, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. washThe organic phases are washed with brine (20 ml
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-834a841f271f4084a12f23e5c60b6a0f
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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