Sodium Hydroxide → 1-(Tert-butoxycarbonyl)-4-phenylpiperidine-3-carboxylic acid

HRID 1276506

반응식

HRID 1276506 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]([C:20]([O:22]C)=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]([C:20]([OH:22])=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 22116087HCID 22116087, 화합물

생성물 1

HCID 221161001-(Tert-butoxycarbonyl)-4-phenylpiperidine-3-carboxylic acid수율 68.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 89 mg of methyl ester (from Example 104, Step B) in 1.5 mL EtOH was added 1.0 mL of 0.5N NaOH. After 36 h the reaction was concentrated under vacuum. The residue was dissolved in 25 mL H2O and washed with 25 mL Et2O. After separating layers, the aqueous phase was acidified to pH 2 using 0.5N KHSO4. The aqueous phase was extracted with 3×25 mL of CH2Cl2. The combined extracts were dried over Na2SO4 and concentrated under vacuum to give 58 mg of a white foam which was taken on without further purification.

후처리

  1. concentrationAfter 36 h the reaction was concentrated under vacuum
  2. dissolutionThe residue was dissolved in 25 mL H2O
  3. washwashed with 25 mL Et2O
  4. customAfter separating layers
  5. extractionThe aqueous phase was extracted with 3×25 mL of CH2Cl2
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-352586b63b9b4c2dbd11530c05137d7d
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166037

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