反応 #44024

反応方程式

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

収率 136.6%

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

収率 136.6%

溶媒

CH2Cl2

反応条件

後処理

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

実験手順

(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.

出典