4-Toluenesulfonyl chloride → tert-BUTOXYCARBONYL-2(R/S)-[3-(4-TOLUENESULFONYLOXY)PROPYL]PIPERIDINE

HRID 392505노트

반응식

HRID 392505 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][CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][CH2:16][O:17][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 10900840Tert-butyl 2-(3-hydroxypropyl)piperidine-1-carboxylate

생성물 1

HCID 23521547tert-BUTOXYCARBONYL-2(R/S)-[3-(4-TOLUENESULFONYLOXY)PROPYL]PIPERIDINE수율 77%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

The title compound from Step B above (2 g, 8.22 mmoles) was dissolved in anhydrous pyridine (10 mL) and the solution was cooled with stirring to 0° C. 4-Toluenesulfonyl chloride (1.88 g, 9.86 mmoles) was added and the mixture was stirred at 0° C. for 2 h. The mixture was evaporated to dryness and the residue was taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate, water, dried (MgSO4), filtered and evaporated to dryness. The product was chromatographed on silica gel using 0.25% methanol in dichloromethane as the eluant to give the title compound (2.53 g, 77%): ESMS: m/z 398.1 (MH+).

후처리

  1. temperaturethe solution was cooled
  2. stirringthe mixture was stirred at 0° C. for 2 h
  3. customThe mixture was evaporated to dryness
  4. washwashed with saturated aqueous sodium bicarbonate, water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe product was chromatographed on silica gel using 0.25% methanol in dichloromethane as the eluant

출처 및 근거

ORD 기록
ord-246ffd5f0854437a84a4fa5f05546ce1
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800636B2

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