Triethylamine → HCID 24984414, Verbindung

3-Prop-2-ynyl-1-oxa-3-aza-spiro[4.5]decan-2-one (55 mg, 0.284 mmol), 4-(4-iodo-benzyl)-morpholine (95 mg, 0.313 mmol), tetrakis(triphenylphosphine)palladium (17 mg, 0.0142 mmol), copper iodide (6 mg, 0.0284 mmol) and triethylamine (0.12 mL, 0.853 mmol) were mixed in acetonitrile (1 mL) under argon. The reaction mixture was stirred at room temperature for 1 hour and then diluted with dichloromethane (6 mL). The mixture was washed with water (4 mL), washed with brine (4 mL), dried over sodium sulfate and concentrated. The residue was purified on silica gel eluting with 10 to 25% ethyl acetate in hexanes. The isolated product was treated with 2M hydrochloric acid in diethyl ether to make the hydrochloric acid salt. The salt was then dissolved in water, washed with hexanes and the aqueous phase then made alkaline using aqueous saturated sodium bicarbonate. The aqueous mixture was then extracted with dichloromethane and the organic phase dried over sodium sulfate and concentrated to give the product as an off-white solid (43 mg, 41%). 1H NMR (300 MHz, CDCl3); δ 7.38 (d, 2H), 7.29 (d, 2H), 4.31 (s, 2H), 3.71 (t, 4H), 3.49 (s, 2H), 3.4 (s, 2H), 2.43 (t, 4H), 1.83 (m, 4H), 1.54 (m, 6H).

1. washThe mixture was washed with water (4 mL)
2. washwashed with brine (4 mL)
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated
5. customThe residue was purified on silica gel eluting with 10 to 25% ethyl acetate in hexanes
6. additionThe isolated product was treated with 2M hydrochloric acid in diethyl ether
7. dissolutionThe salt was then dissolved in water
8. washwashed with hexanes
9. extractionThe aqueous mixture was then extracted with dichloromethane
10. dry with materialthe organic phase dried over sodium sulfate
11. concentrationconcentrated

ORD-Eintrag

ord-2488d39647494ddbac83d24aa006d8a7

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07790717B2