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

HRID 337210ノート

反応式

HRID 337210 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-83da9077a84a4b06b9a4da936f4ea432
出典データセット
uspto-grants-2014_11
特許番号
US08889716B2

反応ノート

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