Cyclopropylamine → Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate

HRID 926027노트

반응식

HRID 926027 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 67126892Ethyl 4-(cyclopropylamino)cyclohexanecarboxylate수율 90.5%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d15fa406e3ce41369fd5e16c7aedd0a9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284295B2

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