tert-Butyl 4-sulfanylpiperidine-1-carboxylate → 4-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 221372

반응식

HRID 221372 반응식
CC([O-])(C)C.[K+].[N:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([CH2:18]OS(C)(=O)=O)[O:15][N:14]=2)=[CH:9][CH:8]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([SH:37])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>C1COCC1.CCOCC>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([S:37][CH2:18][C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:9]=[CH:8][N:7]=[CH:12][CH:11]=3)[N:17]=2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

참가 물질

6

반응물 3

HCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 57954388Methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester

생성물 1

HCID 579544094-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

t-BuOK (92 mg, 823 μmol) and methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester (Preparation 12, 150 mg, 588 μmol) were added to a stirred solution of 4-mercaptopiperidine-1-carboxylic acid tert-butyl ester (191 mg, 881 mol) in anhydrous THF (10 ml). After 100 min, the reaction mixture was diluted with Et2O, before being washed with NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, and concentrated, then the residue was purified by column chromatography (IH-EtOAc, 3:2) to afford the title compound: RT=3.77 min; m/z (ES+)=377.2 [M+H]+.

후처리

  1. washbefore being washed with NaHCO3 and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (IH-EtOAc, 3:2)

출처 및 근거

ORD 기록
ord-bad805c3d4a949ff81a3f21fa38fd134
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207147B2

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