Imidazole → (S)-2-[2-(tert-butyl-dimethyl-silyloxy)-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1963060노트

반응식

HRID 1963060 반응식
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][C@@H:22]1[CH2:27][CH2:28][OH:29])=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][C@@H:22]1[CH2:27][CH2:28][O:29][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])=[O:20])([CH3:17])([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12046236(S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

생성물 1

HCID 67773623(S)-2-[2-(tert-butyl-dimethyl-silyloxy)-ethyl)-piperazine-1-carboxylic acid tert-butyl ester수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Tert-butyl-dimethyl-silyl chloride (3.62 g, 24.02 mmol) and imidazole (3.27 g, 48.03 mmol) were added to a solution of the compound of step 2 (4.609 g, 20.01 mmol) in 75 ml of DCM and the resulting solution was stirred at room temperature for 3 h. The mixture was washed with 50 ml of water and then 50 ml of brine. The aqueous phase was extracted once with DCM. The combined organic phases were dried over sodium sulfate, filtered and evaporated under reduced pressure to give 6.90 g of the title compound as a pale yellow oil.

후처리

  1. washThe mixture was washed with 50 ml of water
  2. extractionThe aqueous phase was extracted once with DCM
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-27cf665530d9482a841b79e0fbebd370
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415336B2

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