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

HRID 906644

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HRID 906644 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-dea2927eacff4db5a585d502ae935fe6
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012995B1

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