Water → HCID 59351187, compound

HRID 555862Notes

Reaction equation

HRID 555862 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[Cl:18][C:19]1[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.O>C1COCC1>[Cl:18][C:19]1[C:24]([C:4]2([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]2)=[N:23][CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 785752,3-DichloropyrazineHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 59351187HCID 59351187, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a vial containing 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (408 mg, 1.678 mmol) and 2,3-dichloropyrazine (250 mg, 1.678 mmol) in THF (2.5 mL) at rt under N2 is added dropwise LiHMDS (1.678 mL, 1.678 mmol). The reaction was stirred at rt 16 h. The reaction mixture was poured into H2O (10 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with saturated NaCl (10 mL), dried (MgSO4), and concentrated. Purification by ISCO (40 g SiO2, 0-75% EtOAc/Hexane) gives 1-tert-butyl 4-methyl 4-(3-chloropyrazin-2-yl)piperidine-1,4-dicarboxylate (565 mg, 1.588 mmol, 95% yield) as a clear, colorless oil. [M+Na]=378.0

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic layers were washed with saturated NaCl (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by ISCO (40 g SiO2, 0-75% EtOAc/Hexane)

Sources & evidence

ORD record
ord-81fd31888c2f46ed9b34ace781f2645b
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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