Diisopropylethylamine → Methyl 1-({5-[(diallylamino)methyl]thien-2-yl}sulfonyl)piperidine-4-carboxylate

HRID 906642ノート

反応式

HRID 906642 の反応式
[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[CH3:27][O:28][C:29](=[O:36])[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14]([N:33]2[CH2:34][CH2:35][CH:30]([C:29]([O:28][CH3:27])=[O:36])[CH2:31][CH2:32]2)(=[O:16])=[O:15])=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotateHCID 113807695-Diallylaminomethyl-thiophene-2-sulfonyl chloride

生成物 1

HCID 67403857Methyl 1-({5-[(diallylamino)methyl]thien-2-yl}sulfonyl)piperidine-4-carboxylate収率 65%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

5-Diallylaminomethyl-thiophene-2-sulfonyl chloride 229b (270 mg, 1.88 mmol) and DIEA (0.88 mL, 5.13 mmol) were dissolved in 10 mL chloroform. This solution was added methylisonipecotate (269 mg, 1.88 mmol) in 1 mL chloroform. The reaction was stirred for 3 h, diluted with CH2Cl2 and extracted with HCl (0.1N), NaHCO3 sat. and brine. The organic layer was dried over MgSO4 and evaporated to dryness. The crude was purified by flash chromatography on silica gel using cyclohexane/EtOAc 1:1 as eluent to obtain 440 mg (65%) of 327a as colorless oil: H′ NMR (CDCl3) δ 7.30 (d, J=3.6 Hz, 1H), 6.83 (d, J=3.6 1H), 5.78 (m, 2H), 5.18 (m, 4H), 3.70 (s, 2H), 3.52 (m, 6H), 3.07 (m, 4H), 2.50 (m, 2H), 2.25 (m, 1H), 1.93 (m, 2H), 1.84 (m, 2H). M/Z APCI: 399.2 (M+1)

後処理

  1. extractionextracted with HCl (0.1N), NaHCO3 sat. and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated to dryness
  4. customThe crude was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-dd04dffdbee14282b9faee6dc920e001
出典データセット
uspto-grants-2011_09
特許番号
US08012995B1

反応ノート

読み込み中…