2-Morpholinoethanol → HCID 136436875, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium bis(trimethylsilyl)amide (180 mg, 0.88 mmol) and 4-(2-hydroxyethyl)morpholine (4 ml) was stirred at 100° C. for 1 hour, then the title compound of Example 26 (100 mg, 0.17 mmol) added and the reaction mixture stirred at 110° C. for 18 hours. The resulting, cool mixture was partitioned between water (10 ml) and dichloromethane (20 ml), the phases separated and the organic phase washed with water (10 ml), dried (MgSO4) and evaporated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel, using an elution gradient of ethyl acetate:methanol (90:10 to 80:20), to yield the title compound (33 mg, 30%) as a white solid. δ (CDCl3): 0.95 (3H, t), 1.04 (3H, t), 1.74 (2H, m), 2.42 (2H, q), 2.56 (4H, m), 2.64 (4H, m), 2.90 (2H, t), 2.99 (2H, t), 3.15 (4H, m), 3.80 (4H, m), 4.75 (2H, t), 5.68 (2H, s), 7.12 (1H, d), 7.25 (1H, m), 7.63 (1H, m), 8.58 (1H, d), 8.62 (1H, s), 8.92 (1H, s), 11.16 (1H, s). LRMS: m/z 652 (M+1)+.

Provenance & Evidence