(3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid → (S)-2-(tert-Butoxycarbonyl)pyrazolidine-3-carboxylic acid

HRID 1396868노트

반응식

HRID 1396868 반응식
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10][N:9]1C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])[CH3:3]>CO.[OH-].[OH-].[Pd+2]>[CH3:4][C:2]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:1])[CH3:3]

참가 물질

4

반응물 1

HCID 68287732(3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid

생성물 1

HCID 58501748(S)-2-(tert-Butoxycarbonyl)pyrazolidine-3-carboxylic acid수율 91%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

To a 100 ml round bottom flask was added (3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (1.84 g, 5.25 mmol) in methanol (30 mL), followed by Pd(OH)2 on carbon (20%, wet) (24.7 mg, 0.035 mmol). The mixture was degassed and stirred under an H2 atmosphere (balloon) at room temperature until LCMS indicated completion of the reaction (1 h). The catalyst was filtered off, and the filtrate was concentrated under vacuum to afford (3S)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (1.03 g, 4.77 mmol, 91% yield) as an off white solid.

후처리

  1. customThe mixture was degassed
  2. customcompletion of the reaction (1 h)
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-a8db6e5acd7c49c98d1e8f1ea838906e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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