تفاعل #80549

معادلة التفاعل

(R)-3-(N,N-Dicyclobutylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran

DMF methanol

carbonmonoxide

triethylamine

→

title compound

المردود 78.0%

Methyl (R)-3-(N,N-Dicyclobutylamino)-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxylate

المردود 78.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىdegassed
2. 2
   أخرىthe reaction mixture was degassed
3. 3
   درجة الحرارةto cool
4. 4
   أخرىthe solvent was removed in vacuo
5. 5
   استخلاصextracted
6. 6
   تجفيفThe combined ether 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,N-Dicyclobutylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran (0.82 g, 1.94 mmol) was dissolved in a solution of DMF/methanol (6:2, 15 mL) and then degassed followed by the inlet of carbonmonoxide (×3). With a slight positive pressure of carbonmonoxide, palladium(II)-acetate (14 mg), 1,3-bis(diphenylphosphino)propane (25 mg) and triethylamine (0.60 mL, 4.3 mmol) were added and the reaction mixture was degassed and subjected to carbonmonoxide once again. The reaction was heated to 70° C. under carbornmonoxide atmosphere with vigorous stirring for 5.5 h. The reaction was allowed to cool and the solvent was removed in vacuo. The remains were taken into a 2M solution of NH3 and then extracted, twice, with diethyl ether. The combined ether portions were dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue. Chromatography on silica (eluent: 12.5% ethyl acetate/hexane) gave 501 mg (78% yield) of the title compound as a clear oil. [α]21D =-138.2° (C=0.1; CHCl3) GC-MS (70 eV) M=333 (4%).

المصدر