Reaktion #624533

Reaktionsgleichung

(E)-tert-butyl 4-cyano-4-(2-(3-ethoxy-3-oxoprop-1-enyl)phenyl)piperidine-1-carboxylate

→

tert-butyl 4-cyano-4-(2-(3-ethoxy-3-oxopropyl)phenyl)piperidine-1-carboxylate

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was degassed with Ar for 2 min
2. 2
   workup.ADDITIONPd/C (10%, 30 mg) was added
3. 3
   SonstigeH2 was bubbled in for a few minutes
4. 4
   FiltrationThe solution was filtered through Celite
5. 5
   Einengenwas concentrated

Vorschrift

(E)-tert-butyl 4-cyano-4-(2-(3-ethoxy-3-oxoprop-1-enyl)phenyl)piperidine-1-carboxylate (21, 278 mg, 0.72 mmol) was dissolved in MeOH (7 mL). The solution was degassed with Ar for 2 min. Pd/C (10%, 30 mg) was added and H2 was bubbled in for a few minutes. The reaction was stirred under a H2 balloon at 23° C. overnight. The solution was filtered through Celite and was concentrated to yield tert-butyl 4-cyano-4-(2-(3-ethoxy-3-oxopropyl)phenyl)piperidine-1-carboxylate. 1H NMR (400 MHz, CDCl3): δ 7.32-7.30 (m, 2H), 7.26-7.24 (m, 2H), 4.28 (bd, 2H), 4.17 (q, 2H), 3.29-3.25 (m, 4H), 2.78-2.74 (m, 2H), 2.34-2.30 (m, 2H), 1.91 (td, 2H), 1.48 (s, 9H), 1.26 (t, 3H). LC/MS RT (5 min method)=2.19 min. Mass observed: 287.22 (M-Boc+H).

Quelle