Reaktion #1244853

Reaktionsgleichung

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

N,N-diisopropylethylamine

TBTU

acetic hydrazide

→

title compound

N′-acetyl-2-[1-(3-chloro-4-cyano-2-methylphenyl)pyrrolidin-2-yl]acetohydrazide

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeLeave
2. 2
   Sonstigethen partition between ethyl acetate and 2N aqueous hydrochloric acid
3. 3
   ExtraktionExtract the organic with 10% (w/w) aqueous sodium carbonate 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 (0.600 g, 2.268 mmol), N,N-diisopropylethylamine (0.876 g, 6.816 mmol) and TBTU (1.092 g, 3.402 mmol) in DMF add a solution of acetic hydrazide (0.252 g, 3.402 mmols) in DMF. Leave to stand for 30 mins then partition between ethyl acetate and 2N aqueous hydrochloric acid. Extract the organic with 10% (w/w) aqueous sodium carbonate solution, then brine. Dry over magnesium sulphate, filter and concentrate under reduced pressure gives the title compound. (0.598 g, 82%) mass spectrum (m/e): 321 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.77 (s, 1H) 7.60 (bs, 1H) 7.40 (d, 1H), 6.88 (d, 1H), 4.35 (t, 1H), 3.86 (m, 1H), 3.04 (m, 1H), 2.51 (m, 1H), 2.44 (s, 3H), 2.00 (s, 3H), 2.22-1.85 (m. 3H).

Quelle