(4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-1H-quinolin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,4,5,6,7,8-hexahydro-1H-quinoline-2-one (0.1 g, 0.66 mmol) in dioxane (10 mL) containing a catalytic quantity (40 μL) was added NaCNBH3 (0.67 g). The reduction was left to stir for 20 hrs at r.t., and then diluted with EtOAc. The organic phase was treated with dilute HCl (3×), and the combined organics were washed with saturated HCO3−, brine, dried over Na2SO4, filtered and concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer). MS (+ES) m/z 254 (M+1)+. The reduction was left the combined organics were washed with saturated HCO3−, brine dried over Na2SO4 filtered concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,4,5,6,7,8-hexahydro-1H-quinoline-2-one (0.1 g, 0.66 mmol) in dioxane (10 mL) containing a catalytic quantity (40 μL) was added NaCNBH3 (0.67 g). The reduction was left to stir for 20 hrs at r.t., and then diluted with EtOAc. The organic phase was treated with dilute HCl (3×), and the combined organics were washed with saturated HCO3−, brine, dried over Na2SO4, filtered and concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer). MS (+ES) m/z 254 (M+1)+. The reduction was left the combined organics were washed with saturated HCO3−, brine dried over Na2SO4 filtered concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,4,5,6,7,8-hexahydro-1H-quinoline-2-one (0.1 g, 0.66 mmol) in dioxane (10 mL) containing a catalytic quantity (40 μL) was added NaCNBH3 (0.67 g). The reduction was left to stir for 20 hrs at r.t., and then diluted with EtOAc. The organic phase was treated with dilute HCl (3×), and the combined organics were washed with saturated HCO3−, brine, dried over Na2SO4, filtered and concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer). MS (+ES) m/z 254 (M+1)+. The reduction was left the combined organics were washed with saturated HCO3−, brine dried over Na2SO4 filtered concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1 g (6.62 mmol) of 3,4,5,6,7,8,-hexahydro-2(1H)-quinolinone, 2.8 g (41 mmol) of sodium formate and 5 mL of formic acid was heated to reflux for 1 day The reaction mixture was then cooled and 20% sodium hydroxide solution was added to make it basic. This mixture was then extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate and the solvent was removed to give a crude product. This was purified on silica gel using ethyl acetate as solvent to provide 752 mg of the desired product with about 10% of the cis-isomer. Recrystallization of this material from cyclohexane did not improve the ratio of the isomers. was heated to reflux for 1 day The reaction mixture was then cooled This mixture was then extracted with ethyl acetate The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate the solvent was removed to give a crude product This was purified on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3,4,5,6,7,8-hexahydro-1H-quinoline-2-one (0.1 g, 0.66 mmol) in dioxane (10 mL) containing a catalytic quantity (40 μL) was added NaCNBH3 (0.67 g). The reduction was left to stir for 20 hrs at r.t., and then diluted with EtOAc. The organic phase was treated with dilute HCl (3×), and the combined organics were washed with saturated HCO3−, brine, dried over Na2SO4, filtered and concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer). MS (+ES) m/z 254 (M+1)+. The reduction was left the combined organics were washed with saturated HCO3−, brine dried over Na2SO4 filtered concentrated to afford the mainly traits product (98 mg, 95%, 15-20% cis isomer)