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Imidazole → Tert-butyl 4-(1H-imidazol-1-YL)piperidine-1-carboxylate

HRID 392501
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HRID 392501 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

생성물 1

HCID 22662911Tert-butyl 4-(1H-imidazol-1-YL)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
60 °C

실험 절차

A solution of the title compound from Step B (4.0 g, 14.32 mmoles) in DMF (120 mL) was added to a stirred solution of NaH (0.52 g, 21.66 mmoles) and imidazole (1.46 g, 21.47 mmoles) in DMF (20 mL) under nitrogen atmosphere. The mixture was stirred at 60° C. for 16 h. DMF was evaporated in vacuo. The resulting crude product was extracted with CH2Cl2 and the extract was successively washed with water and brine, and the CH2Cl2 was evaporated to leave the title residue which was chromatographed on silica gel using 3% (10% cone NH4OH in methanol)-CH2Cl2 as eluant to give the title compound (0.94 g, 26%). FABMS (M+1)=252; δH (CDCl3) 1.4 (s, 9H), 1.6-1.8 (m, 2H), 2.0 (dd, 2H), 2.8 (dt, 2H), 4.05 (m, 1H), 4.2 m, 2H), 6.9 (s, 1H), 7.0 (s, 1H), 7.65 (s, 1H).

후처리

  1. customDMF was evaporated in vacuo
  2. extractionThe resulting crude product was extracted with CH2Cl2
  3. washthe extract was successively washed with water and brine
  4. customthe CH2Cl2 was evaporated

출처 및 근거

ORD 기록
ord-bb3160eb51e34cf0ad408352b27c3d74
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06800636B2

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