Reaktion #1244855

Reaktionsgleichung

1-(3-chloro-4-cyano-2-methylphenyl)proline

N,N-diisopropylethylamine

TBTU

t-butlycarbazate

→

title compound

tert-butyl 2-{[1-(3-chloro-4-cyano-2-methylphenyl)pyrrolidin-2yl]acetyl}hydrazinecarboxylate

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeLeave
2. 2
   Sonstigepartition between ethyl acetate and 10% (w/w) aqueous citric acid
3. 3
   ExtraktionExtract the organic with 2N aqueous sodium hydroxide solution
4. 4
   TrocknenDry over magnesium sulphate
5. 5
   Filtrationfilter
6. 6
   Einengenconcentrate under reduced pressure

Vorschrift

To a solution of 1-(3-chloro-4-cyano-2-methylphenyl)proline (0.623 g, 2.350 mmol), N,N-diisopropylethylamine (1.420 g, 11.750 mmol) and TBTU (1.113 g, 3.530 mmol) in DMF add a solution of t-butlycarbazate (0.462 g, 3.530 mmols) in DMF. Leave to stand for 3 h, then partition between ethyl acetate and 10% (w/w) aqueous citric acid. Extract the organic with 2N aqueous sodium hydroxide solution, then brine. Dry over magnesium sulphate, filter, and concentrate under reduced pressure to obtain the title compound. (0.89 g, 100%) mass spectrum (m/e): 379 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.80 (s, 1H), 7.42 (d, 1H), 6.38 (d, 1H), 6.22 (bs, 1H) 4.33 (t, 1H), 3.88 (m, 1H), 3.04 (m, 1H), 2.81 (m, 3H), 2.53 (m, 1H), 1.85-2.38 (m. 3H), 1.41 (s, 9H).

Quelle