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

HRID 1396868ノート

反応式

HRID 1396868 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a8db6e5acd7c49c98d1e8f1ea838906e
出典データセット
uspto-grants-2014_12
特許番号
US08901119B2

反応ノート

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