Ethyl Acetate → 8-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate

HRID 8748ノート

反応式

HRID 8748 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([O:16]C)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.C([N-]C(C)C)(C)C.[Li+].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH3:24][O:23][C:21]([CH:20]1[CH2:19][CH2:18][C:11]2([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[C:14]1=[O:16])=[O:22]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)2 回HCID 69183850Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate

生成物 1

HCID 219838978-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate収率 110.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate (20.1 g, 0.058 mol) from Step E in tetrahydrofuran (600 mL) at −78° C. was added lithium diisopropylamide mono(tetrahydrofuran) (47 mL, 0.070 mol, 1.5M solution in cyclohexanes). The reaction mixture was stirred at −78° C. for 25 min. Thin layer chromatography (tlc) analysis (50% ethyl acetate in hexanes) showed that starting material remained. Additional lithium diisopropylamide mono(tetrahydrofuran) (31 mL) was added and the reaction mixture was stirred for 20 min. The reaction mixture was poured into saturated ammonium chloride and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated to afford the title compound (19.9 g) which was taken on to the next step without further purification.

後処理

  1. stirringthe reaction mixture was stirred for 20 min
  2. extractionextracted three times with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2199290325e045e6997c103221fdd023
出典データセット
uspto-grants-2006_08
特許番号
US07091211B2

反応ノート

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