反応 #8846

反応方程式

ammonium chloride

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

lithium diisopropylamide mono(tetrahydrofuran)

propionaldehyde

→

clear oil

収率 120.9%

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

収率 120.9%

溶媒

diethyl ether

反応条件

後処理

1. 1
   その他by 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
   抽出extracted three times with diethyl ether
5. 5
   洗浄washed with brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

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).

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