Sodium borohydride → 2-Phenylisobutyric acid

HRID 990220Notes

Reaction equation

HRID 990220 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, and 300 mg of NaBH4 in 25 mL of CH3OH was stirred overnight at room temperature. The mixture was then concentrated in vacuo. The residue was partitioned between EtOAc and H2O. The aqueous portion was treated with concentrated HCl until pH 6, then extracted with EtOAc. The organics were concentrated in vacuo. The residue was dissolved in EtOAc, filtered, and concentrated in vacuo to an oil. The oil was dissolved in CH3OH and concentrated to a solid. The solid was 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 was then concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and H2O
  3. additionThe aqueous portion was treated with concentrated HCl until pH 6
  4. extractionextracted with EtOAc
  5. concentrationThe organics were concentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil
  9. dissolutionThe oil was dissolved in CH3OH
  10. concentrationconcentrated to a solid
  11. filtrationfiltered
  12. washrinsed with EtOAc

Sources & evidence

ORD record
ord-b217415581394e86a87768bc7d1dcd80
Source dataset
uspto-grants-2002_10
Patent number
US06458958B1

Reaction notes

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