1-Bromopentane → Tert-butyl (pentyloxy)carbamate

HRID 1258570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258570
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1CCN2C(=NCCC2)CC1>CC#N>[C:5]([O:4][C:3](=[O:9])[NH:2][O:1][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:8])([CH3:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 80571-BromopentaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 97534tert-butyl N-hydroxycarbamate

Produkt 1

HCID 86653126Tert-butyl (pentyloxy)carbamateAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Tert-butyl hydroxycarbamate (2.1 g, 15.77 mmol, 1 eq.) was dissolved in MeCN and bromopentane (2.73 g, 18.13 mmol, 1.15 eq.) was added followed by DBU (2.52 g, 16.56 mmol, 1.05 eq.). The reaction was stirred at room temperature for 12 h and quenched with 0.1N HCl, extracted with EtOAc, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica gel to give tert-butyl(pentyloxy)carbamate (3.23 g, 91% yield) as a clear oil.

Aufarbeitung

  1. customquenched with 0.1N HCl
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ca8a533c5454482184dfe932440e6a85
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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