Chlorotrimethylsilane → Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate

HRID 335258노트

반응식

HRID 335258 반응식
[Li+].CC([N-]C(C)C)C.[O:9]=[C:10]([CH3:25])[CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:28][Si:27]([CH3:30])([CH3:29])[O:9][C:10](=[CH2:25])[CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 12017169Tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate

생성물 1

HCID 66994845Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate수율 108.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a cooled (−78° C.) solution of LDA (12.3 mL, 24.6 mmol) in THF (50 mL) was added dropwise over 40 minutes a solution of tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate (4.95 g, 20.5 mmol) in THF (20 mL). After an additional 25 minutes, chlorotrimethylsilane (5.21 mL, 41.0 mmol) was added dropwise over 20 minutes. After stirring for an hour, the reaction was poured into saturated NaHCO3 and extracted with ether (2×400 mL). The combined ether layers were washed with brine, dried, filtered and concentrated to afford the title compound (6.95 g, 108% yield) which was used as is in the next step.

후처리

  1. extractionextracted with ether (2×400 mL)
  2. washThe combined ether layers were washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bf909ac08ead4168b866905341c6efb3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883828B2

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