1,2-Dimethoxyethane → tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 341487

Reaktionsgleichung

Reaktionsgleichung von HRID 341487
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=O)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCOC.CC1C=CC(S([CH2:33][N+:34]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([C:33]#[N:34])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 161915Tosylmethyl isocyanideHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 53487658tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (300 mg, 1.33 mmol) was added DME (9 mL) and EtOH (0.2 mL). The mixture was cooled to 0 C when TOSMIC (530 mg, 2.65 mmol) and potassium tert-butoxide (609 mg, 5.2 mmol) were added. The mixture was stirred to room temperature and then heated at 50 C for 18 h. After this time the reaction was evaporated and loaded onto a silica column and eluted with heptane-10% to 30% ethyl actetate to give the title compound (216 mg, 69%). Method B HPLC-MS: MH+ requires m/z=237. Found: m/z=237, Rt=1.35 min (86%).

Aufarbeitung

  1. additionwere added
  2. temperatureheated at 50 C for 18 h
  3. customAfter this time the reaction was evaporated
  4. washeluted with heptane-10% to 30% ethyl actetate

Quellen und Nachweise

ORD-Eintrag
ord-cc049e06862c452cb77dc68bb0597096
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895733B2

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