4-Nitrobenzenesulfonyl chloride → [1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]carbamic acid tert-butyl ester

HRID 337198ノート

反応式

HRID 337198 の反応式
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)([O-:26])=[O:25]>C(Cl)Cl>[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:33]([C:30]2[CH:29]=[CH:28][C:27]([N+:24]([O-:26])=[O:25])=[CH:32][CH:31]=2)(=[O:34])=[O:35])[CH2:19][CH2:18]1)([CH3:13])([CH3:11])[CH3:12]

参加物

5

反応物 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidine

生成物 1

HCID 71079538[1-(4-Nitro-benzenesulfonyl)-piperidin-4-yl]carbamic acid tert-butyl ester収率 92.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Diisopropylethylamine (4.5 ml, 27.0 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (5.0 g, 20.0 mmol) in DCM (40 ml) at room temperature. To this mixture was added 4-nitrophenyl sulfonyl chloride (6.0 g, 27.0 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with DCM (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting solid was collected by filtration, dried with diethyl ether and dried under vacuum give the title compound (7.14 g, 74% yield) as a pale yellow solid. Tr=2.07 min m/z (ES+) (M+Na+) 408.

後処理

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe resulting solid was collected by filtration
  7. dry with materialdried with diethyl ether
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-664feb377bcf4560b78372af9dbb3df8
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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