Benzyl Bromide → 1-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate

HRID 862189노트

반응식

HRID 862189 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)=[O:17])[CH3:14].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:13]([O:15][C:16]([C:18]1([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:20][CH2:19]1)=[O:17])[CH3:14]

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 178418339Butyllithium

생성물 1

HCID 162182711-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate수율 110.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirring solution of diisopropyl amine (38.0 mmol, 3.84 g) in THF (50 mL) cooled to -78° C. was added n-butyl lithium dropwise (41.2 mmol, 16.5 mL of a 1.6M solution in hexanes). To this was added piperidine-1,4-dicarboxylic acid tert-butyl ester ethyl ester (31.7 mmol, 8.16 g) in 20 mL THF. The reaction was allowed to stir for 5 min. and benzyl bromide (31.7 mmol, 5.42 g) was added. The reaction was then allowed to warm to room temperature. The reaction was then diluted with ethyl acetate (200 mL) and washed with 10% KHSO4. The aqueous layers were extracted with ethyl acetate (100 mL). The organics were combined, washed with brine and dried over anhydrous sodium sulfate. The solution was filtered and evaporated under reduced pressure to give 12.13 g of the title compound as a yellow oil.

후처리

  1. washwashed with 10% KHSO4
  2. extractionThe aqueous layers were extracted with ethyl acetate (100 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-6375f2715dde4a28ac8a75d35481e0fe
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05717100

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