Sodium hydride → (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate

HRID 451714

반응식

HRID 451714 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>C1COCC1>[Si:30]([O:29][CH2:28][CH2:27][O:10][C@:8]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1)([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:9])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 59201475(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-hydroxyethyl)piperidine-1-carboxylate

생성물 1

HCID 59201381(R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A mixture of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-hydroxyethyl)piperidine-1-carboxylate (2.5463 g, 7.49 mmol), 60% NaH (2.120 g, 53 mmol), and (2-bromoethoxy)(tert-butyl)dimethylsilane (7.820 g, 32.7 mmol) in THF was heated at 80° C. for 25 h and then cooled to rt. The reaction mixture was then quenched with water and extracted with ethyl acetate (3×), dried over Na2SO4. After the solvent was evaporated under reduced pressure, crude (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate was used directly in the next step without further purification.

후처리

  1. temperaturecooled to rt
  2. customThe reaction mixture was then quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was evaporated under reduced pressure, crude (R)-tert-butyl 3-((R)-1-(2-(tert-butyldimethylsilyloxy)ethoxy)-1-(3-chlorophenyl)ethyl)piperidine-1-carboxylate
  6. customwas used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-f455875ebece43e0b9881a1d802ae920
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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