[Hydroxy(tosyloxy)iodo]benzene → HCID 86722472, compound

3-Methoxy-8-methylene-5,6,7,8-tetrahydroisoquinoline (125) (1.27 g, 7.25 mmol) in a mixture of water (5 mL) and MeOH (45 mL) was treated with [hydroxy(tosyloxy)iodo]benzene (2.84 g, 7.25 mmol) in MeOH (7 mL). After about 30 min water (15 mL) was added then the mixture was concentrated under reduced pressure to remove most of the MeOH. The mixture was basified to about pH 10 with sat. aq. NaHCO3 then EtOAc (˜30 mL) was added. Insoluble material was removed by filtration. The filtrate layers were separated then the aqueous layer was extracted with EtOAc (20 mL). The combined organic solutions were washed with brine (˜25 mL) then dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure then the material was purified on silica gel (40 g) using a gradient from 0-100% EtOAc in heptane. Pure product fractions were combined and concentrated under reduced pressure to yield 3-methoxy-6,7-dihydro-5H-cyclohepta[c]pyridin-8(9H)-one (126) (0.922 g, 67%); LC/MS, method 3, Rt=1.66 min, MS m/z 192 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 6.57 (s, 1H), 3.92 (s, 3H), 3.63 (s, 2H), 2.93-2.85 (m, 2H), 2.61-2.54 (m, 2H), 2.04-1.94 (m, 2H).

1. concentrationthe mixture was concentrated under reduced pressure
2. customto remove most of the MeOH
3. additionEtOAc (˜30 mL) was added
4. customInsoluble material was removed by filtration
5. customThe filtrate layers were separated
6. extractionthe aqueous layer was extracted with EtOAc (20 mL)
7. washThe combined organic solutions were washed with brine (˜25 mL)
8. dry with materialthen dried over MgSO4
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure
11. customthe material was purified on silica gel (40 g)
12. concentrationconcentrated under reduced pressure

ORD record

ord-1b5098b1ddca45308a200ef0f84cf3b4

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193744B2