Acetic Acid → 4-Cyclopropylmorpholine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence