تفاعل #562241

معادلة التفاعل

35

trans-2-phenylcyclopropane-1-carboxylic acid

methoxy(methyl)amine hydrochloride

HATU

DIPEA

→

trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide

المردود 42.0%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe organic phase was extracted with EtOAc (3×1 L)
2. 2
   غسيلthe combined organic layers were washed with water (3×1 L) and brine (1×1 L)
3. 3
   تجفيفdried (Na2SO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue purified by SiO2 chromatography
7. 7
   غسيلeluted with EtOAc/petroleum ether (10 to 50% EtOAc)

الإجراء التجريبي

To a stirred solution of 35 (117.5 g, 724.48 mmol, 1.00 equiv) in DMF (1.2 L) under N2 was added methoxy(methyl)amine hydrochloride (82.3 g, 844.10 mmol, 1.17 equiv), HATU (329 g, 775.58 mmol, 1.07 equiv), and DIPEA (117.5 mL). The reaction mixture was stirred under N2 at 25° C. overnight and then diluted with water (700 mL). The organic phase was extracted with EtOAc (3×1 L), and the combined organic layers were washed with water (3×1 L) and brine (1×1 L), dried (Na2SO4), filtered and concentrated in vacuo. The residue purified by SiO2 chromatography and eluted with EtOAc/petroleum ether (10 to 50% EtOAc) to afford 62.5 g (42%) of trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide (37) as a light yellow oil.

المصدر