Borane → HCID 86747615, compound

Participants

Reaction Conditions

Reaction Steps

2,3-Dihydrobenzofuran-5-acetic acid (0.98 g, 5.5 mmol) and the product from Example 15 (1.21 g, 5.0 mmol) were combined with 1-(3-dmethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.15 g, 6.0 mmol), 1-hydroxybenzotriazole (1.01 g, 67.5 mmol) and triethylamine (5.5 mmol), 0.7 mL) in tetrahydrofuran (50 mL) and the reaction was stirred for 18 hours at 25° C. The product was isolated and treated with 1.0 M borane in tetrahydrofuran (20 mL) at reflux for 4 hours. After isolation of the desired product, treatment with 1.1 equivalents of methanesulfonic acid and recrystallization from ethyl acetate yielded 1.29 g of the desired product as a white solid. m.p. 161°-163° C. 1H NMR (CDCl3, 300 MHz) δ1.7-2.2 (m, 4H), 2.5-3.7 (m, 9H), 2.86 (s, 3H), 3.00 (d, 3 H), 3.18 (t, 2H), 3.81 (s, 3H), 4.55 (t, 2H), 6.71 (m, 3H), 6.94 (dd, 1H), 7.15 (m, 2H), 10.8 (bs, 1H). Anal calcd for C24H33NO5S: C, 64.40; H, 7.43; N, 3.13. Found: C, 64.33; H, 7.36; N, 3.06.

Provenance & Evidence