Sodium Bicarbonate → Methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoate

HRID 1672617Notes

Reaction equation

HRID 1672617 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][CH:4]([CH2:1][OH:2])[CH2:5][C:6]2[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=2)=[CH:23][CH:22]=1)#[N:25]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57831396Methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate

Product 1

HCID 57831349Methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoateYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

24.28 ml of a 1 M borane-THF complex solution (24.28 mmol) are added dropwise to a solution of 5.32 g (77% purity, 12.14 mmol) of methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate from Example 14A in 40 ml of THF at −15° C., and the solution is stirred at this temperature for 4 h. After reaction is complete, saturated sodium bicarbonate solution is added to the reaction mixture, and the solvent is concentrated to dryness. The residue is taken up in dichloromethane, dried over sodium sulfate and, after filtration, again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 2.25 g (55% yield) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. concentrationthe solvent is concentrated to dryness
  3. dry with materialdried over sodium sulfate
  4. filtrationafter filtration
  5. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-e965281d497a40c09a674a3510033bbe
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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