Reaktion #1259577

Reaktionsgleichung

2-(3-cyano-propionyl)-2,5-dimethyl-hex-4-enoic acid ethyl ester

→

2,5-dimethyl-2-pyrrolidin-2-yl-hexanoic acid ethyl ester

Ausbeute 87.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed and hydrogenated under 50 psi of hydrogen gas for 12 h
2. 2
   FiltrationThe reaction mixture was filtered over celite
3. 3
   Einengenthe filtrate was concentrated in vacuo
4. 4
   workup.ADDITIONThe residue was treated with saturated aqueous sodium bicarbonate solution
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   TrocknenThe organic layers were dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A solution of 2-(3-cyano-propionyl)-2,5-dimethyl-hex-4-enoic acid ethyl ester (323 mg, 1.29 mmol) in acetic acid (20 mL) was treated with one drop of 18.0 M aqueous hydrochloric acid solution and platinum oxide (29 mg, 0.129 mmol). The reaction mixture was degassed and hydrogenated under 50 psi of hydrogen gas for 12 h. The reaction mixture was filtered over celite and the filtrate was concentrated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford the desired product, 2,5-dimethyl-2-pyrrolidin-2-yl-hexanoic acid ethyl ester (271 mg, 87%) as a light brown oil. This material was directly used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ: 0.87-0.89 (6H, m), 0.97-1.07 (1H, m), 1.13 (3H, s), 1.15-1.22 (1H, m), 1.24-1.29 (3H, m), 1.38-1.57 (3H, m), 1.67-1.81 (4H, m), 2.86-3.00 (2H, m), 3.28-3.36 (1H, m), 4.11-4.18 (2H, m). LC-MS (ESI) calcd for C14H27NO2: 241.20, found 242.4 [M+H+].

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