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

HRID 602195노트

반응식

HRID 602195 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6120e0c8674240beb93610cabdc551eb
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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