Ammonium Chloride → HCID 178461575, 화합물

HRID 1913549노트

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HRID 1913549 반응식
[CH3:1][C@H:2]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[C:5](=[O:18])[CH2:4][CH2:3]1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([N:36]2[CH:40]=[C:39]([CH:41]=O)[N:38]=[CH:37]2)[CH2:32][CH2:31]1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C@H:2]1[CH2:7][NH:6][C:5](=[O:18])/[C:4](=[CH:41]/[C:39]2[N:38]=[CH:37][N:36]([C@H:33]3[CH2:34][CH2:35][C@H:30]([CH3:29])[CH2:31][CH2:32]3)[CH:40]=2)/[CH2:3]1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 22872605Benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylateHCID 178461291HCID 178461291, 화합물

생성물 1

HCID 178461575HCID 178461575, 화합물수율 55.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate (Org. Lett, 2009, Vol. 11, p. 5410) (772 mg) was dissolved in tetrahydrofuran (15 mL). To the solution, lithium hexamethyldisilazide (LHMDS, 1 N tetrahydrofuran solution, 3.12 mL) was added dropwise at −78° C., and the mixture was stirred for 1 hour. Subsequently, a solution of 1-(trans-4-methylcyclohexyl)-1H-imidazole-4-carbaldehyde (600 mg) in tetrahydrofuran (5 mL) was added dropwise thereto at −78° C., and the mixture was stirred at 0° C. for 3 hours. To the reaction solution, aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate-ethyl acetate/methanol=92/8) to obtain the title compound (500 mg).

후처리

  1. stirringat −78° C., and the mixture was stirred at 0° C. for 3 hours
  2. extractionorganic matter was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a crude product
  7. customThis crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate-ethyl acetate/methanol=92/8)

출처 및 근거

ORD 기록
ord-a4395665ce1a44eeb3e765375bcf5391
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609710B2

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