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

HRID 392505ノート

反応式

HRID 392505 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-246ffd5f0854437a84a4fa5f05546ce1
出典データセット
uspto-grants-2004_10
特許番号
US06800636B2

反応ノート

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