trans-4-benzyltetrahydro-2H-furo[3,4-b][1,4]oxazin-3(4H)-one → trans-4-benzylhexahydro-2H-furo[3,4-b][1,4]oxazine

Temperature

0 °C

To a solution of trans-4-benzyltetrahydro-2H-furo[3,4-b][1,4]oxazin-3(4H)-one (3.1 g, 13.2 mmol) in THF (35 mL) at 0° C. was added BH3:THF (1.0 M in THF; 39.7 mL, 39.7 mmol). The reaction mixture was stirred at 0° C. for 16 hours. The reaction was quenched with aqueous 1 N NaOH solution, adjusting to pH 13, and extracted with EtOAc (100 mL). The organic extract was washed with brine (40 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford trans-4-benzylhexahydro-2H-furo[3,4-b][1,4]oxazine. 1H NMR (400 MHz, CDCl3) δ 7.29-7.31 (m, 5H), 3.96 (t, J=7.2 Hz, 1H), 3.92 (ddd, J=11.6, 3.6, 1.2 Hz, 1H), 3.86 (m, 1H), 3.67-3.77 (m, 2H), 3.52-3.66 (m, 3H), 3.45 (dd, J=12.0, 9.0 Hz, 1H), 3.34 (d, J=13.2 Hz, 1H), 2.71 (ddd, J=12.0, 2.8, 1.2 Hz, 1H), 2.42 (ddd, J=15.6, 8.8, 6.8 Hz, 1H). MS APCl calc'd for C13H17NO2 [M+H]+ 220. found 220.

1. customThe reaction was quenched with aqueous 1 N NaOH solution
2. extractionextracted with EtOAc (100 mL)
3. extractionThe organic extract
4. washwas washed with brine (40 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-949ff8c001d348f2a6b5ab8692651b5d

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846657B2