تفاعل #87109

معادلة التفاعل

water

(R)-methyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate

iodine

3-iodocyclopent-2-enone

→

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(3-oxocyclopent-1-enyl)propanoate

المردود 60.0%

المذيبات

DMF

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at 50° C
2. 2
   درجة الحرارةThe mixture was cooled to ambient temperature
3. 3
   استخلاصThe resulting mixture was extracted with EtOAc (150 mL×3)
4. 4
   تجفيفThe combined organic extracts were dried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=5:1 to 2:1)

الإجراء التجريبي

A solution of (R)-methyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate (32.9 g, 0.100 mol) in DMF (20 mL) was added to a mixture of Zn (19.5 g, 0.300 mol) and iodine (6.6 g, 26 mmol) in DMF (30 mL) under nitrogen protection. The mixture was stirred for 1 h at ambient temperature. Then a solution of 3-iodocyclopent-2-enone (20.8 g, 0.100 mol) in DMF (50 mL), Pd2(dba)3 (2.3 g, 2.5 mmol) and S—Phos (2.1 g, 5.0 mmol) were added successively. The reaction mixture was stirred overnight at 50° C. The mixture was cooled to ambient temperature and water (100 mL) was added. The resulting mixture was extracted with EtOAc (150 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=5:1 to 2:1) to afford (S)-methyl 2-(tert-butoxycarbonylamino)-3-(3-oxocyclopent-1-enyl)propanoate (17 g, 60% yield) as a pale yellow oil.

المصدر