Sodium Iodide → Benzyl 2-cyclohexyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 215943ノート

反応式

HRID 215943 の反応式
Cl[CH2:2][CH2:3][C:4]1([C:20]([O:22]C)=O)[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH:24]1([N:30]2[CH2:2][CH2:3][C:4]3([CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[O:11])[CH2:8][CH2:9]3)[C:20]2=[O:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 588931841-Benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate

生成物 1

HCID 58893180Benzyl 2-cyclohexyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate収率 48.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1-benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate (0.5 g, 0.001 mol), cyclohexanamine (0.18 mL, 0.0016 mol), sodium iodide (0.22 g, 0.0015 mol) and potassium carbonate (0.61 g, 0.0044 mol) in DMF (5.0 mL) was stirred and heated at 120° C. for overnight. Then the reaction mixture was diluted with brine, and extracted with ethyl acetate (3X). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by combiflash (ethyl acetate in hexanes: 40%) to give 180 mg of benzyl 2-cyclohexyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate.

後処理

  1. extractionextracted with ethyl acetate (3X)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by combiflash (ethyl acetate in hexanes: 40%)

出典と根拠

ORDレコード
ord-f6ad03e7e65e49de8e2381d668032cee
出典データセット
uspto-grants-2012_06
特許番号
US08193207B2

反応ノート

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