Acetic Acid → HCID 16755193, compound

Participants

Reaction Steps

A mixture of 0.1 g of (−)-(2R)—N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide, 0.05 g of 2-methoxybenzaldehyde, 0.1 g of sodium triacetoxyborohydride, 0.1 mL of acetic acid and 5 mL of THF was stirred overnight room temperature, then concentrated under reduced pressure. The residue was partitioned between 3×10 mL of ethyl acetate and 10 mL of saturated sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. Preparative TLC eluting with 25% ethyl acetate in hexanes gave the product as a resin: [α]D23° C.=5.7° (c=1.0, MeOH); MS (m+1)=469.3; 1H NMR (500 MHz, CDCl3) 7.34-7.21 (m, 2H), 6.93-6.85 (m, 3H), 6.81-6.71 (m, 2H), 4.64 (m, 1H), 4.41-4.17 (m, 6H), 3.3 (m, 1H), 3.81 (d, 3H), 3.73-3.60 (m, 3H), 3.33-3.16 (m, 1H), 3.01-2.88 (m, 2H), 2.71 (m, 1H), 2.53 (t, 1H) 2.39-2.28 (m, 1H), 2.18 (m, 2H), 1.97 (m, 1H), 0.87 (m, 6H).

Provenance & Evidence