tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 67046469, compound

HRID 606756Notes

Reaction equation

HRID 606756 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.[C:15]([CH2:17][C:18]1[O:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:21][N:22]=1)#[N:16].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[C:15]([C:17](=[C:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:18]1[O:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:21][N:22]=1)#[N:16]

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 3702917HCID 3702917, compound

Product 1

HCID 67046469HCID 67046469, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-Boc-4-piperidone (0.200 g, 1.00 mmol) and 2-(cyanomethyl)-5-phenyl-1,3,4-oxadiazole in dry THF (5 mL), at 5° C. under Ar, was added NaHMDS solution (1M in THF, 1.1 mL, 1.1 mmol) and the mixture was then stirred at room temperature for 16 h. The reaction was quenched with MeOH (1 mL) and then the mixture was evaporated to dryness. The residue was taken up in HCl-dioxane (4 M, 2 mL) and the reaction mixture was kept at room temperature for 20 h before again being evaporated to dryness. The residue was taken up in EtOAc, washed (sat. NaHCO3×2, brine), dried (MgSO4) and evaporated to give the title compound (0.212 g, 80%) as a dark red semi-solid, which was used as such in the next step:

Workup

  1. customThe reaction was quenched with MeOH (1 mL)
  2. customthe mixture was evaporated to dryness
  3. waitthe reaction mixture was kept at room temperature for 20 h
  4. custombefore again being evaporated to dryness
  5. washwashed (sat. NaHCO3×2, brine)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-0b8103f4a46140f382cffca077e808a4
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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