Pyridine → HCID 57905077, compound

SOCl2 (37.1 mL, 509 mmol, 1.3 equiv) was slowly added to a stirred solution of 1,4-dioxaspiro[4.5]decan-8-ylmethanol (67.3 g, 391 mmol) and pyridine (94.8 mL, 1175 mmol, 3 equiv.) in CHCl3 (400 mL) Caution: The reaction is exothermic. The resulting yellow mixture was heated at reflux for 1.5 h and concentrated. The residue was partitioned between water (500 ml) and ether (500 ml). The layers were separated and the aqueous layer was re-extracted with ether (200 ml). The combined ether layers were washed with 1N HCl (2×100 ml), water (200 ml) followed by brine (200 ml), then dried (MgSO4), filtered and concentrated to give the title compound as a dark amber oil (65.7 g, 88% yield). 1H NMR (500 MHz, CDCl3) δ: 3.94 (4 H, t, J=2.9 Hz), 3.41 (2 H, d, J=6.4 Hz), 1.83-1.88 (2 H, m), 1.75-1.79 (2 H, m), 1.63-1.73 (1 H, m), 1.55 (2 H, td, J=4.3, 13.2 Hz), 1.29-1.39 (2 H, m).

1. temperatureThe resulting yellow mixture was heated
2. temperatureat reflux for 1.5 h
3. concentrationconcentrated
4. customThe residue was partitioned between water (500 ml) and ether (500 ml)
5. customThe layers were separated
6. extractionthe aqueous layer was re-extracted with ether (200 ml)
7. washThe combined ether layers were washed with 1N HCl (2×100 ml), water (200 ml)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-045547f21fd140edb54f67b09859a88c

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2