تفاعل #1069808

معادلة التفاعل

(2R)-8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate

3-(3-trifluoromethyl-phenyl)-8-azabicyclo[3.2.1]octan-3-ol

→

yellow oil

المردود 34.4%

8-{[8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}-3-[3-(trifluoromethyl)phenyl]-8-azabicyclo[3.2.1]octan-3-ol

المردود 34.4%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   أخرىthe mixture was partitioned between 400 mL of ethyl acetate and 400 mL of saturated sodium bicarbonate solution
3. 3
   أخرىThe organic phase was removed
4. 4
   غسيلwashed with 400 mL of water
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuum to 1.29 g of a crude oil
8. 8
   أخرىchromatographed on silica gel using 10% methanol in ethyl acetate as eluant

الإجراء التجريبي

(2R)-8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate (0.70 g, 1.8 mmole) and 3-(3-trifluoromethyl-phenyl)-8-azabicyclo[3.2.1]octan-3-ol (0.59 g, 2.4 mmole) were combined in 3 mL of DMSO and heated at 100° C. under nitrogen for 4 hours. After cooling to room temperature, the mixture was partitioned between 400 mL of ethyl acetate and 400 mL of saturated sodium bicarbonate solution. The organic phase was removed, washed with 400 mL of water, dried over magnesium sulfate, filtered and concentrated in vacuum to 1.29 g of a crude oil. The residue was column chromatographed on silica gel using 10% methanol in ethyl acetate as eluant to give 0.30 g of a yellow oil. Crystallization from ethanol/ether with the addition of 0.073 g of fumaric acid gave 0 040 g of the (S)-enantiomer of the title compound as a light yellow solid, m.p. 146-150° C.

المصدر