Sodium Hydroxide → 3-Methoxymethylamino-1-(2-thienyl)propan-1-ol

Participants

Reaction Steps

38.6 g of 3-methoxymethylamino-1-(2-thienyl)-1-propanone hydrochloride salt obtained in Step 1 was dissolved in 115 g of methanol and 40 g of water. The pH value of the resulting solution was adjusted to 11 by addition of 45% NaOH. 2.5 g of sodium borohydride was added, and the mixture was stirred for 1 hour. Afterward the reaction mixture was filtered, concentrated and extracted with 80 g of toluene. The organic layer was concentrated to obtain 33.8 g of 3-methoxymethylamino-1-(2-thienyl)propan-1-ol as an oily product. 1H NMR (400 MHz, CDCl3) δ (ppm)=3.0 (s, 3H), 3.0-3.1 (m, 1H), 4.1 (s, 3H), 4.0-4.1 (m, 3H), 6.1 (dt, J=7.4, 15.4 Hz, 1H), 6.9 (d, J=15.7 Hz, 1H), 7.0 (dd, J=3.7, 5.0 Hz, 1H), 7.1 (d, J=3.4 Hz, 1H).

Provenance & Evidence