Bromocycloheptane → HCID 83225775, compound

Temperature

-10 °C

To a solution of N-(diphenylmethylene)glycerine tert-butyl ester (6.83 mmol) and (R)-4,4-dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphthol[7,6,1,2-cde]azepinium bromide (6.84 μmol) in 45 mL toluene were sequentially added cycloheptyl bromide (8.2 mmol) and CsOH H2O (34.2 mmol) at −10° C. The reaction mixture was stirred at −10° C. for 10 min and then at RT for 4 days. Another portion of (R)-4,4-dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphthol[7,6,1,2-cde]azepinium bromide (6.84 μmol) was added and stirring was continued at RT for another 24 h. The reaction was quenched with water and extracted 3 times with DCM. The combined organic layers were combined, concentrated and the residue was redissolved in 100 mL THF. A solution of 100 mL aq. 0.5M citric acid solution was added and the mixture was stirred at RT for 4 h. The mixture was concentrated to half of its volume and extracted twice with Et2O. The aqueous layer was basified with solid NaHCO3 and extracted 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to obtain the desired product as yellow oil.

1. customat −10° C
2. waitat RT for 4 days
3. stirringstirring
4. waitwas continued at RT for another 24 h
5. customThe reaction was quenched with water
6. extractionextracted 3 times with DCM
7. concentrationconcentrated
8. dissolutionthe residue was redissolved in 100 mL THF
9. additionA solution of 100 mL aq. 0.5M citric acid solution was added
10. stirringthe mixture was stirred at RT for 4 h
11. concentrationThe mixture was concentrated to half of its volume
12. extractionextracted twice with Et2O
13. extractionextracted 3 times with DCM
14. dry with materialThe combined organic layers were dried over MgSO4
15. concentrationconcentrated in vacuo

ORD record

ord-ee2553f03891449da37615849d9a222f

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409917B2