تفاعل #80555

معادلة التفاعل

CHCl3

BBr3

(R)-3-(N-Cyclobutyl-N-isopropylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran hydrochloride

→

title compound

المردود 98.0%

(R)-3-(N-Cyclobutyl-N-isopropylamino)-8-fluoro-5-hydroxy-3,4-dihydro-2H-1-benzopyran

المردود 98.0%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded dropwise
2. 2
   أخرىThe cooling-bath was removed and after 2 h at room temperature the reaction
3. 3
   workup.ADDITIONThe reaction was poured out onto an ice/2M NH3 solution
4. 4
   أخرىthe CH2Cl2 portion was separated
5. 5
   استخلاصthe aqueous layer re-extracted
6. 6
   تجفيفThe combined CH2Cl2 portions were dried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىthe solvent removed in vacuo
9. 9
   أخرىto give the crude residue

الإجراء التجريبي

(R)-3-(N-Cyclobutyl-N-isopropylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran hydrochloride (1.76 g, 5.34 mmol) was dissolved in anhydrous CH2Cl2 (45 mL) and cooled to -40° C. To the solution was BBr3 (1.3 mL, 13.4 mmol), dissolved in anhydrous CH2Cl2 (7 mL), added dropwise. The cooling-bath was removed and after 2 h at room temperature the reaction was complete. The reaction was poured out onto an ice/2M NH3 solution and the CH2Cl2 portion was separated, the aqueous layer re-extracted, twice, with CH2Cl2. The combined CH2Cl2 portions were dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue. Chromatography on silica (eluent: 30% ethyl acetate/hexane) gave 1.46 g (98% yield) of the title compound as a gum [α]21D =-95.7° (C=0.1; CHCl3) GC-MS (70 eV) M=279 (0.7%). The hydrochloride salt was made by dissolving the pure base in ether and dropping an excess of an ethereal HCl solution. The salt was washed with diethyl ether to give a white solid Mp: 120° C. sinters.

المصدر