Cyclopropylamine → Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate

HRID 926027ノート

反応式

HRID 926027 の反応式
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.ClCCCl.C(O)(=O)C>[CH:1]1([NH:4][CH:20]2[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 69828CyclopropylamineHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 67126892Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate収率 90.5%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

To a mixture of 3.35 g of cyclopropylamine, 1.0 mL of acetic acid, 9.34 g of sodium triacetoxyborohydride, and 30 mL of 1,2-dichloroethane was added dropwise 5.00 g of ethyl 4-oxocyclohexane carboxylate at room temperature. After stirring at room temperature for 14 hours, to the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution to quench the reaction. To the reaction mixture was added chloroform, followed by extraction and then the organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (aqueous ammonia-methanol-chloroform) to obtain 5.62 g of ethyl 4-(cyclopropylamino)cyclohexane carboxylate as a colorless oily substance.

後処理

  1. customto quench
  2. customthe reaction
  3. extractionfollowed by extraction
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (aqueous ammonia-methanol-chloroform)

出典と根拠

ORDレコード
ord-d15fa406e3ce41369fd5e16c7aedd0a9
出典データセット
uspto-grants-2016_03
特許番号
US09284295B2

反応ノート

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