Acetonitrile → Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate

HRID 656957

Reaktionsgleichung

Reaktionsgleichung von HRID 656957
Br[CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CN(C=O)C>[C:8]1([CH2:7][O:6][C:5]([NH:4][CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:19][CH2:20]2)=[O:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 278694benzyl N-(2-bromoethyl)carbamate2×HCID 7238334-(N-Boc-amino)piperidine

Produkt 1

HCID 22989976Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamateAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of phenylmethyl (2-bromoethyl)carbamate (12.9 g, 50 mmol) (prepared from phenylmethyl (2-bromoethyl)carbamate and phenylmethyl chloridocarbonate according to the method of A. J. Brouwer and R. M. J. Liskamp, European Journal of Organic Chemistry (2005), (3), 487-495), 1,1-dimethylethyl 4-piperidinylcarbamate (10 g, 50 mmol), potassium carbonate (6.9 g, 50 mmol), acetonitrile (100 ml) and DMF (30 ml) was heated at 40° C. for 2.5 days. The solvents were decanted from inorganic residues and evaporated. The residue was partitioned between ethyl acetate and dilute brine. The organic extract was dried (MgSO4) and evaporated affording a white solid (17.6 g, 93%).

Aufarbeitung

  1. customThe solvents were decanted from inorganic residues
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and dilute brine
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2be4e431668143509c580027eb637861
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

Verknüpfte Notizen

Wird geladen…