Acetic Acid → Tert-butyl 4-carbamimidoylpiperidine-1-carboxylate

HRID 419706ノート

反応式

HRID 419706 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[NH:17])[NH:15]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[H][H]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[NH:15])[NH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 178418361HCID 178418361、化合物HCID 178451986HCID 178451986、化合物

生成物 1

HCID 44828660Tert-butyl 4-carbamimidoylpiperidine-1-carboxylate収率 114.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Dissolve 4-(N-Hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (9.7 g 1.00 equiv; 39.9 mmoles) in methanol (300 mL) and add acetic acid (2 equiv, 79.73 mmoles; 4.6 mL), and methanol washed Raney Nickel (2.7 g). Heat the reaction to 50° C., then hydrogenate with 1 ATM hydrogen gas for 4.5 hours. Filter the reaction mixture through Celite and concentrate under reduced pressure. Suspend the solid in diethyl ether, filter and dry under reduced pressure to give 10.39 g of 4-carbamimidoyl-piperidine-1-carboxylic acid tert-butyl ester.

後処理

  1. washwashed Raney Nickel (2.7 g)
  2. temperatureHeat
  3. customthe reaction to 50° C.
  4. filtrationFilter the reaction mixture through Celite
  5. concentrationconcentrate under reduced pressure
  6. filtrationfilter
  7. customdry under reduced pressure

出典と根拠

ORDレコード
ord-e6789619158c43e48ac3e8cf85a31415
出典データセット
uspto-grants-2012_01
特許番号
US08093383B2

反応ノート

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