Formic Acid → (2S,5R)-1-Boc-2,5-dimethylpiperazine

HRID 1038560ノート

反応式

HRID 1038560 の反応式
C([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:10]([CH3:22])[CH2:9]1)C1C=CC=CC=1.C(O)=O>CO.[C].[Pd]>[CH3:22][C@H:10]1[CH2:9][NH:8][C@H:13]([CH3:14])[CH2:12][N:11]1[C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16]

参加物

5

反応物 2

HCID 284Formic AcidHCID 66598992(2S,5R)-4-Benzyl-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 11745988(2S,5R)-1-Boc-2,5-dimethylpiperazine収率 101.1%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

(2S,5R)-tert-butyl 4-benzyl-2,5-dimethylpiperazine-1-carboxylate (3.11 g, 10.2 mmol) was dissolved in methanol (19 mL), added palladium carbon (156 mg) under an argon atmosphere, and added formic acid (2.4 g, 51.1 mmol) under ice-cold conditions. The solution was reverted to room temperature, and stirred overnight. Then, the reaction solution was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The obtained residue was added water and hexane, and extracted. An aqueous solution of sodium hydroxide was added to the aqueous layer, extracted with 2-methyltetrahydrofuran, dried over anhydrous sodium sulfate, concentrated in vacuo, and the title compound (2.21 g (yield >100%)) was obtained as a colorless oil.

後処理

  1. customwas reverted to room temperature
  2. filtrationThen, the reaction solution was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe obtained residue was added water and hexane
  5. extractionextracted
  6. additionAn aqueous solution of sodium hydroxide was added to the aqueous layer
  7. extractionextracted with 2-methyltetrahydrofuran
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7ef19673402e4c90b27aeb4de2f175a9
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

反応ノート

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