Methanol → HCID 69942605, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-N,N-diisopropyl-3-[5-(2-carbamoylethyl)-2-hydroxyphenyl]-3-phenylpropanamine (obtained in Example 25), (0.50 g, 1.31 mmol) in ethanol (15 mL) and H2O (10 mL) was added KOH (3.75 g, 66.8 mmol). The mixture was stirred overnight at 100° C. The solvent was evaporated and the residue redissolved in H2O and washed with diethyl ether. The aqueous layer was acidified with conc. HCl and the precipitate was collected by filtration and washed with 2 M HCl. The product was fractionated on a reversed-phase PEP RPC HR 30/26 (Pharmacia Biotech AB, Sweden) column using a gradient of 20-60% acetonitrile with 0.1% TFA. Fractions were pooled and hydrochloric acid (2 mL, conc.) was added and the solvent was evaporated. The residue was crystallised from methanol-diethyl ether to give 0.37 g (0.96 mmol, 74%); 1H NMR (CD3OD) δ1.28 (m, 12H), 2.48 (m, 4H), 2.76 (t, 2H), 3.04 (t, 2H), 3.67 (m, 2H), 4.39 (t, 1H), 6.72 (d, 1H), 6.92 (d, 1H), 7.00 (s, 1H), 7.19 (t, 1H), 7.32 (m, 4H); mp. 205-207° C.; [α]D +3.7° (c=1.0, methanol). Anal. (C24H33NO3*1.0HCl) C, H, N.

Provenance & Evidence