Piperidine → (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate

HRID 720036노트

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HRID 720036 반응식
[C:1]([O-:4])([O-:3])=O.[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].[CH2:24]1COC[CH2:25]1.O>>[CH2:24]([O:3][C:1]([C@H:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=[O:4])[CH3:25]

참가 물질

5

반응물 4

HCID 8082PiperidineHCID 10387Benzyl chloroformate2회HCID 11430Potassium CarbonateHCID 21881883Oxolane--water (1/1)

생성물 1

HCID 40634406(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate수율 100%

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온도
0 °C

실험 절차

A 250 mL round-bottom flask was charged with K2CO3 (13.5 g, 97.6 mmol), piperidine (10 g, 32.5 mmol), and a 1:1 mixture of THF/H2O (100 mL). A 50 mL addition funnel was placed on the flask and charged with CbzCl (6.67 g, 39.0 mmol). The flask was cooled to 0° C. and then CbzCl was added dropwise over 5 minutes. The reaction mixture was warmed to 20° C. and stirred for 12 h. The reaction mixture was extracted with EtOAc (250 mL) and the organic layer was washed with saturated NaCl (250 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material (9.5 g, 100% yield) was carried on without further purification.

후처리

  1. additionA 50 mL addition funnel
  2. temperatureThe reaction mixture was warmed to 20° C.
  3. extractionThe reaction mixture was extracted with EtOAc (250 mL)
  4. washthe organic layer was washed with saturated NaCl (250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-296690d55ed54cb588bebbcaf1061682
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132551B2

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