2-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonate → tert-BUTOXYCARBONYL-2(R/S)-[2-(1H-IMIDAZOL-1-YL)ETHYL]PIPERIDINE

HRID 392503노트

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HRID 392503 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[Na]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 230901662-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonateHCID 57373095Imidazole sodium

생성물 1

HCID 23521542tert-BUTOXYCARBONYL-2(R/S)-[2-(1H-IMIDAZOL-1-YL)ETHYL]PIPERIDINE수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

The title compound from Step B above (2.68 g, 8.72 mmoles) (crude product, prior to chromatography) was dissolved in anhydrous DMF (30 mL) and sodium imidazole (1.18 g, 13.1 mmoles) was added. The mixture was heated at 70° C. for 2 h and then evaporated to dryness. The product was directly chromatographed on silica gel using 1% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (1.69 g, 69%): ESMS: m/z 280.1 (MH+); dH (CDCl3) 1.48 ppm (9H, s, CH3); dC (CDCl3) CH3: 28.5, 28.5, 28.5; CH2: 19.1, 25.5, 28.9, 31.8, ˜39.1, 44.3; CH: 48.1, 118.9, 129.5, 137.1; C: 80.1, carbonyl not visible.

후처리

  1. customevaporated to dryness
  2. customThe product was directly chromatographed on silica gel using 1% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

출처 및 근거

ORD 기록
ord-06cec6602d824474b50d5a35adbad18b
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800636B2

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