Bromocycloheptane → HCID 83225775, compound

Temperature

-10 °C

To a soln. 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 comb. org. layers were combined, conc. and the residue was redissolved in 100 mL THF. A soln. of 100 mL aq. 0.5 M citric acid soln. 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 comb. org. layers were dried over MgSO4 and conc. 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. dissolutionconc. and the residue was redissolved in 100 mL THF
8. additionwas added
9. stirringthe mixture was stirred at RT for 4 h
10. concentrationThe mixture was concentrated to half of its volume
11. extractionextracted twice with Et2O
12. extractionextracted 3 times with DCM
13. dry with materiallayers were dried over MgSO4 and conc. in vacuo

ORD record

ord-c5c50696398443d4b3dda35695577549

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388198B2