Hexane → 1-Benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine

HRID 602195ノート

反応式

HRID 602195 の反応式
C([Li])CCC.CCCCCC.[I-].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]([CH2:26][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[C:23]([CH3:25])[N:24]=2)=[CH:16][CH:15]=1.[CH2:46]([O:53][C:54]([N:56]1[CH2:61][CH2:60][CH2:59][CH:58]([CH:62]=O)[CH2:57]1)=[O:55])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>O1CCCC1.O>[CH2:46]([O:53][C:54]([N:56]1[CH2:61][CH2:60][CH2:59][CH:58]([CH:62]=[CH:26][C:22]2[S:21][C:20]([C:17]3[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=3)=[N:24][C:23]=2[CH3:25])[CH2:57]1)=[O:55])[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 9899653Benzyl 3-formylpiperidine-1-carboxylateHCID 86615887[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methyltriphenylphosphonium iodideHCID 178418339Butyllithium

生成物 1

HCID 672674511-Benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine収率 87.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

In an argon atmosphere, a solution of 1.59 mol/Ln-butyl lithium in hexane (2.03 mL, 3.23 mmol), chilled to −78° C., was added to a suspension of [2-(4-chlorophenyl)-4-methylthiazol-5-yl]methyltriphenylphosphonium iodide (1.80 g, 2.94 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred for 1 hour as it warmed from −78° C. to room temperature. Subsequently, the mixture was chilled again to −78° C. and 1-benzyloxycarbonyl-3-formylpiperidine (727 mg, 2.94 mmol) in tetrahydrofuran (5 mL) was added. The mixture was stirred at −78° C. for 1 hour and at room temperature for the subsequent 6 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate and washed with brine. The washed product was dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 1.16 g (87%) of the desired compound as a yellow oil.

後処理

  1. temperaturewarmed from −78° C. to room temperature
  2. stirringThe mixture was stirred at −78° C. for 1 hour and at room temperature for the subsequent 6 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe washed product was dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

出典と根拠

ORDレコード
ord-6120e0c8674240beb93610cabdc551eb
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

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