Triethylamine → HCID 71279909, Verbindung

HRID 246161Notizen

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14](=O)[NH2:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>ClCCl.O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]#[N:15])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

In a 25 mL round bottomed flask (cis-3-carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (1.00 g, 4.13 mmol) was suspended in dichlormethane (7 mL). The suspension was cooled to −10° C. in an acetone-dry ice bath. To the cooled suspension was added slowly triethylamine (1.15 mL, 8.25 mmol) and subsequently TFAA (0.62 mL, 4.39 mmol) so that the temperature is maintained. The reaction mixture was stirred at that temperature for 3 h and then diluted with water and dichloromethane. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 60% EtOAc in heptane) to afford 0.803 g (87%) of cis-(3-cyano-cyclohexyl)-carbamic acid tert-butyl ester as a white crystalline solid. 1H NMR (300 MHz, DMSO-d6) δ: 6.86 (d, J=7.9 Hz, 1H), 3.09-3.30 (m, 1H), 2.77 (tt, J=12.0, 3.3 Hz, 1H), 2.04 (d, J=12.1 Hz, 1H), 1.90 (d, J=9.1 Hz, 1H), 1.61-1.80 (m, 2H), 1.37 (s, 9H), 1.21-1.35 (m, 3H), 0.98-1.20 (m, 1H).

Aufarbeitung

temperatureis maintained
washThe organic layer was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 0% to 60% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag: ord-b314fd5289e549de8e86bb6ada1dc50d
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658646B2

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