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Ethanol hydrochloride → 1-[1-({5-[(Diallylamino)methyl]thien-2-yl}sulfonyl)piperidin-4-yl]heptan-1-one

HRID 906644
ノート
印刷プレビュー

反応式

HRID 906644 の反応式
[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14]([N:17]2[CH2:22][CH2:21][CH:20]([C:23](N(OC)C)=[O:24])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[CH2:29]([Li])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].Cl.CCO>C1COCC1>[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14]([N:17]2[CH2:18][CH2:19][CH:20]([C:23](=[O:24])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22]2)(=[O:16])=[O:15])=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 21887872Ethanol hydrochlorideHCID 867613991-({5-[(diallylamino)methyl]thien-2-yl}sulfonyl)-N-methoxy-N-methylpiperidine-4-carboxamideHCID 178506865HCID 178506865、化合物

生成物 1

HCID 674035001-[1-({5-[(Diallylamino)methyl]thien-2-yl}sulfonyl)piperidin-4-yl]heptan-1-one収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

反応条件

温度
-20 °C

実験手順

327b (376 mg, 0.88 mmol) was dissolved in anhydrous THF and cooled to −20° C. To this solution was added dropwise at −20° C. hexyllithium (2M in hexane) (2.46 mL, 6.2 mmol). The reaction was allowed to warm to rt. during 3 h and poured on 100 mL HCl/EtOH (5%). The aqueous phase was extracted with CH2Cl2 and the combined organic layers are washed with NaOH (2N) and brine, dried over MgSO4 and evaporated to dryness. The crude material was purified by flash chromatography on silica gel using cyclohexane/EtOAc 4:1 as eluent to obtain 186 mg (47%) of (327c) as a brownish oil: H1 NMR (CDCl3) δ 7.40 (d, J=3.6 Hz, 1H), 725 (d, J=3.6 1H), 5.95 (m, 2H), 5.50 (m, 4H), 4.32 (s, 2H), 3.70-3.50 (m, 6H), 2.50 (m, 2H), 2.32 (m, 3H), 1.85 (m, 2H), 1.68 (m, 2H), 1.46 (m, 2H), 0.130-1.12 (m, 6H), 0.80 (t, J=6.6 Hz, 3H), M/Z APCI: 453.2 (M+1)

後処理

  1. temperatureto warm to rt
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. washthe combined organic layers are washed with NaOH (2N) and brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe crude material was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-dea2927eacff4db5a585d502ae935fe6
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012995B1

反応ノート

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