Benzoin → 2-Cyanoethyl 1-{[(alpha-Benzoylbenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 227343

Reaktionsgleichung

Reaktionsgleichung von HRID 227343
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]([CH2:20][C:21]1([CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[C:18]=[O:19]>C1(C)C=CC=CC=1>[C:7]([CH:9]([O:10][C:18]([NH:17][CH2:20][C:21]1([CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 8400BenzoinHCID 85863752HCID 85863752, Verbindung

Produkt 1

HCID 668108572-Cyanoethyl 1-{[(alpha-Benzoylbenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane AcetateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of benzoin (0.599 mmol) and 2-cyanoethyl 1-isocyanatomethyl-1-cyclohexane acetate (7) (0.599 mmol) in 10 mL of anhydrous toluene was refluxed overnight. The reaction mixture was concentrated and the residue purified on silica gel (40% ethyl acetate in hexane) to afford 230 mg (83%) of the title compound. 1H NMR (CDCl3): δ 7.95 (2H, dd, J=8.2, 1.4 Hz); 7.50-7.46 (3H, m); 7.41 (5H, m); 6.84 (1H, s); 5.40 (1H, t, J=6.8 Hz); 4.26 (2H, m); 3.24 (2H, d, J=6.8 Hz); 2.68 (2H, dt, J=2.4, 6.4 Hz); 2.36 (2H, d, J=1.2 Hz); 1.52-1.37 (10H, m).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified on silica gel (40% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c44f774cb0754c1bb0ffd2ef25f5d2be
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560483B2

Verknüpfte Notizen

Wird geladen…