Lithium Hydroxide → 1-Phenylpiperidine-4-carboxylic acid

HRID 1177973노트

반응식

HRID 1177973 반응식
[Li+].[OH-].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6]>C1COCC1.CO.O>[C:13]1([N:10]2[CH2:11][CH2:12][CH:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 59559569Methyl 1-phenylpiperidine-4-carboxylate

생성물 1

HCID 30239901-Phenylpiperidine-4-carboxylic acid수율 67.3%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

LiOH (43 mg, 1.03 mmol) was added to a stirred solution of 1-phenyl-piperidine-4-carboxylic acid methyl ester (150 mg, 0.68 mmol) in THF:MeOH:H2O (3:1:1, 3.2 mL), and the resulting mixture was stirred at room temperature overnight. The MeOH and THF were evaporated and the residue was diluted with water (2 mL), acidified with citric acid solution and the product extracted with EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated in vacuo to afford 94 mg (67.1% yield) of 1-Phenyl-piperidine-4-carboxylic acid. LCMS purity: 95.9%.

후처리

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionthe product extracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1646ac55394c4c3e8f6b5aca11154fcd
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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