Sodium borohydride → 2-Phenylisobutyric acid

HRID 133684

반응식

HRID 133684 반응식
OC1(C(C2C=CC=CC=2)C2C=CC=CC=2)CCCCN1CCCC([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)=O.[BH4-].[Na+]>CO>[CH3:24][C:19]([C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)([CH3:23])[C:20]([OH:22])=[O:21]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 867606954-[4-(Hydroxydiphenylmethyl-1-piperidinyl]-1-oxobutyl]-alpha,alpha-dimethylphenylacetic acid

생성물 1

HCID 132222-Phenylisobutyric acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 4-[4-[4-(hydroxydiphenylmethyl-1-piperidinyl]-1-oxobutyl]-α,α-dimethylphenylacetic acid, prepared in accordance with Example 12, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-a493c1fff8a5433bb01556ea8fd4ec99
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390906B2

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