تفاعل #1726688

معادلة التفاعل

3B

6-(4-(Azetidin-3-yloxy)benzyl)-2-oxa-6-azaspiro[3.3]heptane

ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate

→

3

المردود 61.0%

(3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

المردود 61.0%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   أخرىsealed
2. 2
   أخرىThe solid mixture was melted in a preheated oil bath
3. 3
   ترشيحthe mixture was filtered
4. 4
   أخرىpurified by preparative RP HPLC (gradient: 15-55% acetonitrile over 25 min, 0.2% ammonia buffer)
5. 5
   أخرىevaporated
6. 6
   workup.ADDITIONDichloromethane was added
7. 7
   أخرىthe solution was dried (phase separator)
8. 8
   تركيزconcentrated in vacuo

الإجراء التجريبي

3B (0.30 g, 1.15 mmol) was mixed with ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.30 g, 1.38 mmol) in a microwave vial and sealed. The solid mixture was melted in a preheated oil bath and stirred at 120° C. for 4 h. DMSO (2 mL) was added and the mixture was filtered, and then purified by preparative RP HPLC (gradient: 15-55% acetonitrile over 25 min, 0.2% ammonia buffer). The pure fractions were combined and then evaporated. Dichloromethane was added and the solution was dried (phase separator) and concentrated in vacuo. There was obtained 0.30 g (61%) of 3 as a colorless oil. The oil gradually solidified on standing in room temperature. 1H NMR (500 MHz, CDCl3): δ 3.38 (s, 4H), 3.49 (s, 2H), 4.31 (d, 1H), 4.65 (m, 1H), 4.73 (s, 5H), 5.06 (m, 1H), 5.11 (m, 1H), 6.72 (d, 2H), 7.19 (d, 2H), 7.47-7.63 (m, 3H), 8.14 (d, 2H), MS (APCI+) m/z 433 [M+H]+, LC purity: 97%.

المصدر