تفاعل #44024

معادلة التفاعل

Dimethylcarbamoyl chloride

(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol

(8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol

triethylamine

N2

→

112

المردود 136.6%

(8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamate

المردود 136.6%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction stirred for 18 hours
2. 2
   تركيزThe reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water
3. 3
   workup.ADDITIONwere added
4. 4
   استخلاصThe aqueous layer was extracted with several more portions of EtOAc
5. 5
   غسيلThe combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol (111; 1.19 g, 3.18 mmol) and triethylamine (2.21 ml, 15.9 mmol) were added to CH2Cl2 (15 mL) in a flame-dried flask and placed tinder N2. DMAP (77.8 mg, 0.637 mmol) was added and the mixture stirred for 5 minutes. Dimethylcarbamoyl chloride (0.88 mL, 1.54 mmol) was added dropwise and the reaction stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water were added. The aqueous layer was extracted with several more portions of EtOAc. The combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine, dried over Na2SO4 and concentrated to yield 940 mg of 112 as a yellow oil. The material was purified by column chromatography using EtOAc/hexanes gradients to yield 836 mg (59%) of a mixture of cis/trans isomers.

المصدر