Reaktion #617830

Reaktionsgleichung

(S)-2-[bromo-(6-methoxy-pyridin-3-yl)-methyl]-morpholine-4-carboxylic acid tert-butyl ester

→

(R)-2-(6-Methoxy-pyridin-3-ylmethyl)-morpholine-4-carboxylic acid tert-butyl ester

Ausbeute 88.6%

Lösungsmittel

methanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction mixture
2. 2
   Filtrationfiltered through Dicalite
3. 3
   WaschenThe filtrate was washed with 1M sodium hydroxide
4. 4
   ExtraktionThe aqueous phase was extract 2 times with ethyl acetate
5. 5
   WaschenThe combined organic phase was washed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

(S)-2-[bromo-(6-methoxy-pyridin-3-yl)-methyl]-morpholine-4-carboxylic acid tert-butyl ester (290 mg, 0.75 mmol) was dissolved in methanol (5 mL) and hydrogenated at 0.25 bar in the presence of 50 mg 10% Pd/C. Reaction mixture was diluted with ethyl acetate and filtered through Dicalite. The filtrate was washed with 1M sodium hydroxide. The aqueous phase was extract 2 times with ethyl acetate. The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated to afford (R)-2-(6-Methoxy-pyridin-3-ylmethyl)-morpholine-4-carboxylic acid tert-butyl ester (205 mg, 88%) as a light yellow oil. Chiral HPLC (Chiralpak-AD) indicated that product was 98.3% pure. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45 (s, 9H) 2.53-2.79 (m, 3H) 2.86-3.00 (m, 1H) 3.38-3.58 (m, 2H) 3.73-3.89 (m, 3H) 3.91 (s, 3H) 6.68 (d, J=8.33 Hz, 1H) 7.39-7.49 (m, 1H) 8.00 (d, J=2.15 Hz, 1H).

Quelle