Tert-butyl 4-(hydrazinecarbonyl)-4-methylpiperidine-1-carboxylate → 4-(5-Isopropyl-(1,3,4)oxadiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 400432Notes

Reaction equation

HRID 400432 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]([NH:17][NH2:18])=[O:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>COC(OC)(OC)C(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[O:16][C:2]([CH:1]([CH3:4])[CH3:3])=[N:18][N:17]=2)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 66678033Tert-butyl 4-(hydrazinecarbonyl)-4-methylpiperidine-1-carboxylate

Product 1

HCID 866860364-(5-Isopropyl-(1,3,4)oxadiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl esterYield 105.3%

Reagents, catalysts & solvents 1

HCID 404951,1,1-Trimethoxy-2-methylpropaneSolvent

Procedure

30 g 4-hydrazinocarbonyl-4-methyl-piperidine-1-carboxylic acid tert-butyl ester was refluxed with 150 mL 1,1,1-trimethoxy-2-methyl-propane overnight. The excess of reagent was removed under vacuum and the residue was purified by chromatography on silica gel to give 19 g of the desired product.

Workup

  1. customThe excess of reagent was removed under vacuum
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-6f8b740d41f34358974a24fb4e422016
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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