Sodium hydride → 1,1-Dimethylethyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-piperidinecarboxylate

HRID 1867374Notes

Reaction equation

HRID 1867374 reaction equation
[C:1](=[N:4][OH:5])([NH2:3])[CH3:2].[H-].[Na+].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21](OCC)=O)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[NH4+].[Cl-]>C1COCC1>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[O:5][N:4]=[C:1]([CH3:2])[N:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 30926N-HydroxyacetamidineHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 210983601,1-Dimethylethyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-piperidinecarboxylateYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution 1.30 g (17.49 mmol) of acetamide oxime in 55 ml THF was treated with 0.76 g (17.49 mmol) of NaH (55% in oil) and the corresponding suspension stirred for 45 min at RT. 3.00 g (11.66 mmol) of ethyl 1-tert-butoxycarbonylpiperidine-4-carboxylate dissolved in 15 ml of THF was added and heated at 65° C. for 2 h. The solution was cooled to RT, poured on aqueous saturated NH4Cl solution and extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% KHSO4, dried (Na2SO4) and evaporated to give 2.19 g (70%) of the title compound as orange liquid. MS: 268.2 (MH+).

Workup

  1. additionwas added
  2. temperatureheated at 65° C. for 2 h
  3. temperatureThe solution was cooled to RT
  4. extractionextracted with Et2O (3×)
  5. washThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% KHSO4
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-6daae288f7d048728ce9c7dc1cdf11db
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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