Lithium Hydroxide → 1-((Tert-butoxy)carbonyl)-4,4-difluoropiperidine-2-carboxylic acid

HRID 74900

반응식

HRID 74900 반응식
[F:1][C:2]1([F:19])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:4]([C:15]([O:17]C)=[O:16])[CH2:3]1.[OH-].[Li+]>C1COCC1.CO.O>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C:2]([F:1])([F:19])[CH2:3][CH:4]1[C:15]([OH:17])=[O:16])=[O:9])([CH3:14])([CH3:12])[CH3:13]

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 497612851-Tert-butyl 2-methyl 4,4-difluoropiperidine-1,2-dicarboxylate2회

생성물 1

HCID 101069001-((Tert-butoxy)carbonyl)-4,4-difluoropiperidine-2-carboxylic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-tert-butyl 2-methyl 4,4-difluoropiperidine-1,2-dicarboxylate, 13e, (4.6 g, 16.5 mmol) in THF (18 mL), methanol (18 mL) and H2O (9 mL) was added lithium hydroxide (3.45 g, 82.22 mmol). The reaction mixture was stirred at room temperature for 1 hour. All volatiles were removed under reduced pressure. The residue was diluted with a slight amount of water and ether. The layers were separated and the organic phase was discarded. The aqueous phase was acidified to pH 3 with the addition of aqueous saturated KHSO4 solution. The product was extracted with EtOAc. The organic phase was washed with water, dried over MgSO4, filtered and evaporated to dryness. The resulting product was used without further purification.

후처리

  1. customAll volatiles were removed under reduced pressure
  2. additionThe residue was diluted with a slight amount of water and ether
  3. customThe layers were separated
  4. additionThe aqueous phase was acidified to pH 3 with the addition of aqueous saturated KHSO4 solution
  5. extractionThe product was extracted with EtOAc
  6. washThe organic phase was washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe resulting product was used without further purification

출처 및 근거

ORD 기록
ord-20b677953a494242ab1dc23acc184e4c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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