4-Methylmorpholine → trans-2-(4-Methyl-cyclohexylcarbamoyl)-cyclopropanecarboxylic acid methyl ester

HRID 456516ノート

反応式

HRID 456516 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[C:8]([OH:10])=O)=[O:4].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.CN1CCOCC1.[CH3:40][C@H:41]1[CH2:46][CH2:45][C@H:44]([NH2:47])[CH2:43][CH2:42]1>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[C:8](=[O:10])[NH:47][CH:44]1[CH2:45][CH2:46][CH:41]([CH3:40])[CH2:42][CH2:43]1)=[O:4]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12510972rac-(1R,2R)-2-(methoxycarbonyl)cyclopropane-1-carboxylic acidHCID 178461305HCID 178461305、化合物

生成物 1

HCID 68456814trans-2-(4-Methyl-cyclohexylcarbamoyl)-cyclopropanecarboxylic acid methyl ester収率 95.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Stir a solution of trans-cyclopropane-1,2-dicarboxylic acid monomethyl ester (Example 3a) (3.0 g, 20.8 mmol) and TOTU (8.5 g, 26 mmol) in DMF (300 mL) at ambient temperature for 20 min at which time add N-methylmorpholine (2.4 mL 22.9 mmol) and trans 4-methylcyclohexylamine 3.06 g, 27.0 mmol). After 3 h, remove the solvent and dissolve the residue in H2O/EtOAc. Extract the aqueous layer 3 more times with EtOAc and combine the extracts. Wash the extract with saturated NaHCO3 solution, brine and dry over MgSO4. Concentrate the solvent to afford the crude product, and purify by column chromatography over silica gel to give 4.76 g (95%) of colorless crystals, m/z=240 (M+H)+.

後処理

  1. customremove the solvent
  2. dissolutiondissolve the residue in H2O/EtOAc
  3. extractionExtract the aqueous layer 3 more times with EtOAc
  4. washWash the
  5. extractionextract with saturated NaHCO3 solution, brine
  6. dry with materialdry over MgSO4
  7. concentrationConcentrate the solvent
  8. customto afford the crude product
  9. custompurify by column chromatography over silica gel

出典と根拠

ORDレコード
ord-ef05b5e889744b17b5b358d93891ff24
出典データセット
uspto-grants-2007_03
特許番号
US07186724B2

反応ノート

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