Water → Tert-butyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate

HRID 585479Notes

Reaction equation

HRID 585479 reaction equation
[BH4-].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][C:12](=[N:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].O>O1CCCC1>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([NH:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 28123BorohydrideHCID 20824233Tert-butyl 4-[(tert-butoxycarbonyl)hydrazono]piperidine-1-carboxylate

Product 1

HCID 20824232Tert-butyl 4-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 ml of a solution of borohydride in tertahydrofurane (1.0 mol/l) is slowly added to a solution of 0.12 mole of 4-(tert-butoxycarbonyl-hydrazono)-piperidine-1-carboxylic acid tert-butyl ester (compound 5 g) in 100 ml of dry tetrahydrofurane. After complete addition, the mixture is stirred for another 30 min after which a 100 ml of water is added to destroy the excess of borohydride. Subsequently the tetrahydrofurane is evaporated and the resulting aqeous solution extracted with diethyl ether. After drying the solvent over magnesium sulfate, the ether is evaporated. M. p. 112-115° C.

Workup

  1. additionAfter complete addition
  2. additionis added
  3. customto destroy the excess of borohydride
  4. customSubsequently the tetrahydrofurane is evaporated
  5. extractionthe resulting aqeous solution extracted with diethyl ether
  6. dry with materialAfter drying the solvent over magnesium sulfate
  7. customthe ether is evaporated

Sources & evidence

ORD record
ord-9ba28d6429c24a299a4a7433cfc2ea0e
Source dataset
uspto-grants-2005_08
Patent number
US06933296B2

Reaction notes

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