HCID 25129100, compound → HCID 25128746, compound

A mixture of 12 (90 mg, 0.44 mmol) and a catalytic amount of 10% Pd/C in EtOAc (3 mL) was stirred at 23° C. under a hydrogen atmosphere for 3 h. After this time, the catalyst was filtered off through a pad of Celite and the filtrate was concentrated under reduced pressure to afford (R)-3-[(2-methoxyethoxy)methoxy]oxepane (83 mg, 92%) as a colourless oil: 1H NMR (CDCl3) δ 4.70 (d, J=7.2 Hz, 1H), 4.67 (d, J=7.2 Hz, 1H), 3.83-3.58 (m, 7H), 3.50 (t, J=4.6 Hz, 2H), 3.34 (s, 3H), 1.72-1.67 (m, 1H), 1.46-1.44 (m, 4H), 1.22-1.19 (m, 1H); 13C NMR (CDCl3) δ 93.9, 76.5, 73.7, 71.8, 71.6, 66.7, 58.8, 32.6, 30.7, 20.9. A mixture of the above compound (50 mg, 0.24 mmol) and 6 N HCl (0.5 mL) in THF (2 mL) was stirred at 23° C. for 16 h. The solvent was removed and the aqueous phase was extracted with CHCl3. The organic extracts were washed with a saturated solution of NaHCO3, dried (Na2SO4) and the solvent was removed. The residue was purified by flash-chromatography (1:4 EtOAc/CHCl3) to afford 8e (24 mg, 84%) as a colourless oil: [α]D20=−4.2 (c 0.8, CHCl3); 1H NMR (CDCl3) δ 3.87-3.85 (m, 1H), 3.76-3.62 (m, 4H), 2.37 (bs, 1H), 1.78-1.65 (m, 5H), 1.54-1.52 (m, 1H); 13C NMR (CDCl3) δ 73.2, 70.7, 70.4, 36.4, 30.0, 20.2.

1. filtrationAfter this time, the catalyst was filtered off through a pad of Celite
2. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-c7ae6cfafefa41d5b13f8dfa18319bdf

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501961B2