Tert-butyl (piperidin-4-ylmethyl)carbamate → benzyl N-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]piperidine-1-carboximidoyl]carbamate

HRID 1585483

Reaktionsgleichung

Reaktionsgleichung von HRID 1585483
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][C:24]([NH:26][C:27](=[NH:30])SC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:27](=[NH:30])[NH:26][C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

Produkt 1

HCID 140391597benzyl N-[4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]piperidine-1-carboximidoyl]carbamateAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

7.8 g (36.4 mmole) of 4-(N-tert-butyloxycarbonylaminomethyl) piperidine and 8.98 g (40 mmole) of N-benzyloxycarbonyl-S-methylisothiourea was mixed in 25 mL ethanol. The mixture was heated at 60-70° C. for six hours and left at roomtemperature for two days. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic layer was washed twice with 0.3 M KHSO4 and once with brine. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using a stepwise gradient of CH2Cl2 /MeOH (100/0, 97/3, 95/5, 90/10) as eluent to yield 5.22 g (37%) of the title product.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washThe organic layer was washed twice with 0.3 M KHSO4 and once with brine
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f6bab3beffce4d6296742112544967dd
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939392

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