تفاعل #595416

معادلة التفاعل

tert-butyl 8-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

potassium hydroxide

2-(phenoxymethyl)oxirane

→

tert-butyl 8-bromo-5-(2-hydroxy-3-phenoxypropyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

المردود 21.0%

المذيبات

acetone

EtOAc

ظروف التفاعل

المعالجة

1. 1
   أخرىcondensed
2. 2
   غسيلwashed twice with water
3. 3
   تجفيفThe organic layer was then dried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   أخرىcondensed
6. 6
   أخرىThe crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N)

الإجراء التجريبي

A solution of tert-butyl 8-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (449.7 mg, 1.28 mmol) and powdered potassium hydroxide (86.9 mg, 1.54 mmol) in acetone (4.0 ml) was stirred for 15 minutes before the addition of 2-(phenoxymethyl)oxirane (254 mg, 1.69 mmol). After 1 h the reaction was condensed, diluted with EtOAc and washed twice with water and then brine. The organic layer was then dried over Na2SO4, filtered and condensed. The crude mixture was purified by silica gel chromatography (1% MeOH/CH2Cl2+0.1% Et3N). Yield=21%. ESI (m/z): 546.6 (M+CHCOO−).

المصدر