Lithium hydroxide, monohydrate → Di-tert-butyl 1-(1-acetylpiperidin-4-yl)hydrazine-1,2-dicarboxylate

HRID 875149Notes

Reaction equation

HRID 875149 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[N:11](C(=O)C2C=CC=CC=2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.O>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68934227Di-tert-butyl 1-(1-acetylpiperidin-4-yl)-2-benzoylhydrazine-1,2-dicarboxylate

Product 1

HCID 57444162Di-tert-butyl 1-(1-acetylpiperidin-4-yl)hydrazine-1,2-dicarboxylateYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

45 g (0.1 mol) of di-tert-butyl 1-(1-acetylpiperidin-4-yl)-2-benzoylhydrazine-1,2-dicarboxylate were dissolved in 1 L of tetrahydrofuran and a solution of 5.8 g (0.14 mol) of lithium hydroxide monohydrate in 1 L of water were added. The mixture was stirred at room temperature for 16 hours, the tetrahydrofuran removed in vacuo and the aqueous layer extracted several times with dichloromethane. The organic phase was dried over sodium sulfate and evaporated to dryness, giving 32 g (84% yield) of the title compound.

Workup

  1. customthe tetrahydrofuran removed in vacuo
  2. extractionthe aqueous layer extracted several times with dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4c7a9cff1c084cc29ea17994ba2332f0
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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