تفاعل #580812

معادلة التفاعل

iodine

benzyl (2R,5E)-2-[bis(tert-butoxycarbonyl)amino]-6-nitrohex-5-enoate

diethyl ether

1-bromo-2,3-dichlorobenzene

magnesium

diethyl ether

→

title compound

(3R,6S)-3-Amino-1-(2-methoxyethyl)-6-phenylazepan-2-one

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThis mixture was refluxed for 3 h
2. 2
   أخرى2.0 mL of the Grignard solution prepared
3. 3
   workup.ADDITIONabove was added
4. 4
   workup.ADDITIONAfter 1 and 2 h, respectively, 2.0 and 1.0 mL of the Grignard solution was added
5. 5
   أخرىThe reaction was quenched with a saturated aqueous solution of ammonium chloride
6. 6
   أخرىthe phases separated
7. 7
   غسيلthe organic phase washed with saturated aqueous sodium potassium tartrate and brine
8. 8
   تجفيفThe combined organics were dried over magnesium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated
11. 11
    أخرىto give a residue that
12. 12
    أخرىwas purified by silica gel chromatography (0%→3% methanol/dichloromethane)

الإجراء التجريبي

To a slurry of 1-bromo-2,3-dichlorobenzene (1.46 g, 6.46 mmol) in diethyl ether (10 mL) was added magnesium (0.157 g, 6.46 mmol) and a crystal of iodine. This mixture was refluxed for 3 h, and then cooled to room temperature. A solution of benzyl (2R,5E)-2-[bis(tert-butoxycarbonyl)amino]-6-nitrohex-5-enoate (0.50 g, 1.08 mmol) in diethyl ether (10 mL) was cooled to 0° C., and 2.0 mL of the Grignard solution prepared above was added. After 1 and 2 h, respectively, 2.0 and 1.0 mL of the Grignard solution was added. The reaction was quenched with a saturated aqueous solution of ammonium chloride, the phases separated and the organic phase washed with saturated aqueous sodium potassium tartrate and brine. The combined organics were dried over magnesium sulfate, filtered and concentrated to give a residue that was purified by silica gel chromatography (0%→3% methanol/dichloromethane) to give the title compound (0.52 g). MS 411.0 (M+1-2Boc).

المصدر