Ammonium Chloride → HCID 178461575, compound

HRID 1913549Notes

Reaction equation

HRID 1913549 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 178461575HCID 178461575, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a4395665ce1a44eeb3e765375bcf5391
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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