2-Cyclohepten-1-one → HCID 15643612, 화합물

온도

-65 °C

(S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine (348.4 mg, 1.60 mmol) was dissolved in ether (12 mL) and n-butyl lithium (2.5M in hexanes, 0.61 mL, 1.53 mmol) was added to the solution at -65° C. The solution was stirred for 5 min at -65° C., gradually (for 20 min) warmed to 0° C. and stirred for 10 min at 0° C. To a second flask was added CuI (254 mg, 1.33 mmol) and 10 mL of diethyl ether. This solution was cooled to -40° C. and treated with n-butyl lithium (0.51 mL, 1.28 mmol). The solution in the first flask was cooled to -35° C. and added via canula to the solution of n-BuCu in the second flask. The resulting solution was stirred for 15 min at -35° C., for 10 min at -30° C., and cooled to -78° C. After 30 min, 2-cycloheptenone (141 mg, 1.28 mmol) was added slowly at -78° C. The reaction mixture was quenched after 1 hr by adding 4N NH4Cl (15 mL) at -78° C. and extracted with ether (20 mL). The extract was washed with 1N HCl (15 mL), dried (Na2SO4) and concentrated. The oily residue was purified by column chromatography on silica gel (10:1=hexanes/ethyl acetate) to afford (S)-3-n-butylcycloheptanone (136 mg, 63% chemical yield, 96% ee, [α]D =-33.0 (c= 3.2, chloroform)).

1. temperaturegradually (for 20 min) warmed to 0° C.
2. stirringstirred for 10 min at 0° C
3. temperatureThis solution was cooled to -40° C.
4. temperatureThe solution in the first flask was cooled to -35° C.
5. additionadded via canula to the solution of n-BuCu in the second flask
6. stirringThe resulting solution was stirred for 15 min at -35° C., for 10 min at -30° C.
7. temperaturecooled to -78° C
8. waitAfter 30 min
9. customThe reaction mixture was quenched after 1 hr
10. additionby adding 4N NH4Cl (15 mL) at -78° C.
11. extractionextracted with ether (20 mL)
12. washThe extract was washed with 1N HCl (15 mL)
13. dry with materialdried (Na2SO4)
14. concentrationconcentrated
15. customThe oily residue was purified by column chromatography on silica gel (10:1=hexanes/ethyl acetate)

ORD 기록

ord-9e64563bec07459890a0f68d8023c2d3

출처 데이터셋

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05134238