反応 #74400

反応方程式

LDA

2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one

1-bromo-2-(2-bromoethoxy)ethane

→

title compound

2-((1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino)-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one

溶媒

THF

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   抽出it was extracted with EtOAc
4. 4
   洗浄The organic layer was washed with sat'd NH4Cl
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude residue was purified through flash chromatography (4:1:0.05; CH2Cl2/EtOAc/MeOH)

実験手順

To the mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one (840 mg, 4.0 mmol) in THF (5.0 mL) was added LDA (2.0 M, 20 mL) at −78° C. The resulting mixture was stirred for 10 min at −78° C., and then 1-bromo-2-(2-bromoethoxy)ethane (3.71 g, 16 mmol) was added. The mixture was allowed to warm to room temperature and then stirred overnight. A sat'd solution of NaH2PO4 was added, and it was extracted with EtOAc. The organic layer was washed with sat'd NH4Cl, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified through flash chromatography (4:1:0.05; CH2Cl2/EtOAc/MeOH) to give the title compound as off-white solid. MS (ES+): 281 (M+H)+.

出典