2-amino-1-(furan-2-yl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7.0 g of α-(aminomethyl)-2-furan-methanol and 7.5 g of 2,3-dihydro-2,2-dimethyl-6-(2-bromoethoxy)-4H-1,3-benzoxazin-4-one is melted and the melt is stirred for 1 hour in a bath at about 110°. 50 ml of isopropanol and 2 ml of concentrated ammonia solution are added to the reaction mixture whilst this is still warm, the mixture is boiled for 5 minutes and filtered and the filtrate is allowed to cool. After working up, α-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethyl]-aminomethyl]-2-furanmethanol with a melting point of 169°-171° is obtained. this is still warm the mixture is boiled for 5 minutes filtered to cool

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in a similar manner to Example 3 starting from 2-(4-(5-cyanopyridin-3-yl)phenyl)-2-methylpropanoic acid (example 21a) and 2-amino-1-(furan-2-yl)ethanol. Yield: 75%. 1H NMR (400 MHz, DMSO): δ 1.41 (s, 6H), 3.26 (m, 1H), 3.41 (m, 1H), 4.63 (t, 1H), 5.45 (br-s, 1H), 6.21-6.22 (d, 1H), 6.35 (t, 1H), 7.34 (t, 3H), 7.35-7.37 (dd, 2H), 7.54-7.55 (d, 1H), 7.71-7.73 (dd, 2H), 8.61 (t, 1H), 8.97-8.98 (d, 1H), 9.15-9.16 (d, 1H). MS (M+H, 358).