Acetic Acid → HCID 86713716, compound

A solution of 2-(benzyloxy)cyclobutanone (prepared according to the method of P. Bisel et al., Eur. J. Org. Chem. 1998, 4, 729-733; 2.35 g, 13.3 mmol) and 2-aminoethanol (1.63 g, 26.7 mmol) in dichloromethane (47 mL) was treated with acetic acid (0.76 mL, 13.3 mmol) and sodium triacetoxyborohydride (5.95 g, 26.7 mmol) and stirred at room temperature for 16 hours. Aqueous sodium hydroxide solution (1 N, 100 mL) was added and the mixture was extracted with dichloromethane (2×100 mL). The combined organic layers were washed with aqueous sodium hydroxide solution (1 N, 100 mL), dried over magnesium sulfate and concentrated in vacuo to afford the product as a colorless oil. Yield: 2.9 g, 13 mmol, 98%. 1H NMR (400 MHz, CDCl3) δ 7.28-7.39 (m, 5H), 4.51 (AB quartet, JAB=11.7 Hz, ΔνAB=61.1 Hz, 2H), 4.13-4.18 (m, 1H), 3.54-3.58 (m, 2H), 3.32-3.39 (m, 1H), 2.72-2.78 (m, 2H), 2.5 (ν br s, 2H), 2.05-2.14 (m, 1H), 1.83-1.98 (m, 3H).

1. extractionthe mixture was extracted with dichloromethane (2×100 mL)
2. washThe combined organic layers were washed with aqueous sodium hydroxide solution (1 N, 100 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated in vacuo

ORD record

ord-a0dba59b1eb04dee86c6bd44082884e9

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916564B2