تفاعل #721035

معادلة التفاعل

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

acetic acid 2-(2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-ylmethyl)-9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-1-yl ester

n-hexane

ethyl acetate

→

(3R,6S)-[6-(9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-ylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

المردود 24.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىsolvent is evaporated
2. 2
   استخلاصthe residue is extracted with dichloromethane (3×100 mL)
3. 3
   تجفيفThe combined organic layers are dried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىto give a crude product that
7. 7
   أخرىis purified by column chromatography (silica gel, eluent

الإجراء التجريبي

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (833 mg, 3.67 mmol, 5.0 eq) is added at room temperature to a stirred solution of acetic acid 2-(2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-ylmethyl)-9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-1-yl ester (360 mg, 0.73 mmol, 1.0 eq) in toluene (60 mL). After 2 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3×100 mL) and a saturated sodium carbonate aqueous solution (100 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: n-hexane:ethyl acetate, 10:1 to 1:1, v/v) to afford (3R,6S)-[6-(9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-ylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester as a light yellow solid (75 mg, 24% yield).

المصدر