Triethylamine → cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

HRID 931302노트

반응식

HRID 931302 반응식
C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.CC1CCNCC1C(OCC)=O.C(N(CC)CC)C.[CH3:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]>ClCCl>[CH3:35][C@H:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:46])[CH3:47])=[O:43])[CH2:38][C@H:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 13658603Ethyl 4-methylpiperidine-3-carboxylateHCID 707916011-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

생성물 1

HCID 131735164cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate수율 83.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Di-tert-butyl dicarbonate (3.26 g, 15.20 mmol) was added to a solution of ethyl 4-methylpiperidine-3-carboxylate (2.0 g, 11.68 mmol) and triethylamine (3.9 mL, 28.05 mmol) in anhydrous dichloromethane (50 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The mixture partitioned between dichloromethane and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a mixture of the cis and trans diastereomers of 1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (3.0 g). The crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether) to afford cis-1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (2.5 g).

후처리

  1. customThe mixture partitioned between dichloromethane and water
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford
  6. customThe crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-4a634299e5f74e8d8bc683344d04df11
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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