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

HRID 215943노트

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HRID 215943 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

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온도
120 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-f6ad03e7e65e49de8e2381d668032cee
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193207B2

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