반응 #8846

반응 방정식

ammonium chloride

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate

lithium diisopropylamide mono(tetrahydrofuran)

propionaldehyde

→

clear oil

수율 120.9%

tert-Butyl 2-(1-hydroxyprop-1-yl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

수율 120.9%

용매

diethyl ether

반응 조건

후처리

1. 1
   기타by evaporating with toluene (10 mL) three times in vacuo
2. 2
   workup.DISSOLUTIONdissolved in tetrahydrofuran (100 mL)
3. 3
   workup.WAITAfter 5 min
4. 4
   추출extracted three times with diethyl ether
5. 5
   세척washed with brine
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Step G (4.5 g, 17.8 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in tetrahydrofuran (100 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (24 mL, 36 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 30 min at −78° C. before adding propionaldehyde (2.6 mL, 36 mmol). After 5 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (4.75 g).

출처