Ethanol → [1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 337210노트

반응식

HRID 337210 반응식
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[Cl-].[NH4+]>[Fe].O>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 71079538[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]carbamic acid tert-butyl ester

생성물 1

HCID 43819146[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester수율 82.2%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.5 g, 1.3 mmol) was suspended in a 5:1 mixture of ethanol and water (20 ml). To this solution was added iron powder (0.22 g, 3.4 mmol) followed by saturated ammonium chloride solution (3 ml) and the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to room temperature and filtered through a pad of celite, the celite was washed with ethanol (10 ml) and EtOAc (50 ml) and the solution was concentrated under vacuum. The resulting residue was suspended in water (10 ml) and the solid precipitate collected by filtration and dried under vacuum to give the title compound (0.38 g, 78% yield) as a white solid. Tr=1.84 min, m/z (ES+) (M+Na)+ 378.

후처리

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washthe celite was washed with ethanol (10 ml) and EtOAc (50 ml)
  4. concentrationthe solution was concentrated under vacuum
  5. filtrationthe solid precipitate collected by filtration
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-83da9077a84a4b06b9a4da936f4ea432
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

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