Acetic Acid → 4-Cyclopropylmorpholine-3-carboxamide

Temperatur

70 °C

To 1.2 g (7.2 mmol) of morpholine-3-carboxamide hydrochloride (a synthesis of which is described in WO-2005/026 156, Hennequin L. F. A. et al.) dissolved in methanol (36 ml) are successively added 2.9 g of 3 Å molecular sieves, 4.3 g (72 mmol) of acetic acid, 7. g (43.2 mmol) of 2-[(1-ethoxycyclopropyl)oxy]trimethylsilane and 4.4 g (31.7 mmol) of sodium cyanoborohydride. The reaction mixture is heated at 70° C. for 3 hours 30 minutes, and then cooled to room temperature and filtered. The filtrate is concentrated under reduced pressure and the residue is then taken up in dichloromethane (200 ml) and washed three times with aqueous NaOH solution (1N) (100 ml). The organic phase is dried over Na2SO4, filtered and then concentrated under reduced pressure. 0.58 g of product is obtained, in the form of a white powder. Yield 47%. Melting point 116° C. MH+: 171.2 (tr: 1.03 min., condition 1).

1. temperaturecooled to room temperature
2. filtrationfiltered
3. concentrationThe filtrate is concentrated under reduced pressure
4. washwashed three times with aqueous NaOH solution (1N) (100 ml)
5. dry with materialThe organic phase is dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-aec08d966e864370b0f77c65e3762a5a

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08436011B2