Sodium borohydride → 2-Phenylisobutyric acid

HRID 227598Notes

Reaction equation

HRID 227598 reaction equation
OC(C1C=CC=CC=1)(C1C=CC=CC=1)C1CCN(CCCC([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=2)=O)CC1.[BH4-].[Na+]>CO>[CH3:25][C:20]([C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)([CH3:24])[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 99356992-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 132222-Phenylisobutyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylphenylacetic acid, prepared in accordance with Example 13, and 300 mg of NaBH4 in 25 mL of CH3OH is stirred overnight at room temperature. The mixture is then concentrated in vacuo. The residue is partitioned between EtOAc and H2O. The aqueous portion is treated with concentrated HCl until pH 6, then extracted with EtOAc. The organics are concentrated in vacuo. The residue is dissolved in EtOAc, filtered, and concentrated in vacuo to an oil. The oil is dissolved in CH3OH and concentrated to a solid. The solid is slurried with EtOAc, filtered, and rinsed with EtOAc to afford 4-[4-[4-hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetic acid.

Workup

  1. concentrationThe mixture is then concentrated in vacuo
  2. customThe residue is partitioned between EtOAc and H2O
  3. additionThe aqueous portion is treated with concentrated HCl until pH 6
  4. extractionextracted with EtOAc
  5. concentrationThe organics are concentrated in vacuo
  6. dissolutionThe residue is dissolved in EtOAc
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil
  9. dissolutionThe oil is dissolved in CH3OH
  10. concentrationconcentrated to a solid
  11. filtrationfiltered
  12. washrinsed with EtOAc

Sources & evidence

ORD record
ord-9dcfd2779ad94dfaae807881b3932142
Source dataset
uspto-grants-2009_07
Patent number
US07560561B2

Reaction notes

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