1-Bromo-2-Chloroethane → 1-Benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate

HRID 215942노트

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HRID 215942 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1.Br[CH2:32][CH2:33][Cl:34]>O1CCCC1>[Cl:34][CH2:33][CH2:32][C:14]1([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12][N:11]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 78491-Bromo-2-ChloroethaneHCID 15125441-Benzyl 4-methyl piperidine-1,4-dicarboxylateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 588931841-Benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Lithium bis(trimethylsilyl)amide (LiHMDS) in THF (1.0 M, 7.2 mL, 0.0072 mol) was added to a solution of 1-benzyl 4-methyl piperidine-1,4-dicarboxylate (1.00 g, 0.00360 mol) in tetrahydrofuran (10.0 mL) at −78° C. The reaction mixture had been stirred at −78° C. for 1 hr, then 1-bromo-2-chloroethane (0.45 mL, 0.0054 mol) was slowly added to the mixture. The reaction mixture was allowed to warm to room temperature and stirred for 2 hrs. The reaction was quenched with saturated NH4Cl, extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, concentrated. The residue was flash chromatographed (ethyl acetate in hexane: 20%) to afford 1-benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hrs
  3. customThe reaction was quenched with saturated NH4Cl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (ethyl acetate in hexane: 20%)

출처 및 근거

ORD 기록
ord-a415cabdb7e14f55bef4e499903a0012
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193207B2

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