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

HRID 419706노트

반응식

HRID 419706 반응식
[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]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 178418361HCID 178418361, 화합물HCID 178451986HCID 178451986, 화합물

생성물 1

HCID 44828660Tert-butyl 4-carbamimidoylpiperidine-1-carboxylate수율 114.6%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e6789619158c43e48ac3e8cf85a31415
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093383B2

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