Methanol → HCID 56965816, compound

HRID 1931576Notes

Reaction equation

HRID 1931576 reaction equation
O.[NH2:2][NH2:3].[C:4]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].CO.[BH4-].[Na+]>C(O)C>[C:7]([O:6][C:4]([N:11]1[CH2:16][CH2:15][CH:14]([NH:2][NH2:3])[CH2:13][CH2:12]1)=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 56965816HCID 56965816, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (100 mL, ˜2 mol) was added to a solution of 1-Boc-4-piperidone (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 20.0 g, 100 mmol) in ethanol (180 mL) under nitrogen at room temperature and the reaction mixture was stirred at room temperature overnight. Methanol (180 mL) was added and the reaction mixture was cooled to 0-5° C. Sodium borohydride (14.2 g, 375 mmol) was added in portions and the reaction mixture was allowed to warm to room temperature and stir for 2 h. The solvents were evaporated under reduced pressure, dichloromethane was added and the mixture was washed with water, dried (sodium sulfate), filtered, and evaporated to give 4-hydrazino-piperidine-1-carboxylic acid tert-butyl ester (18.9 g, 88%) as a viscous oil, which was used for the next step without further purification.

Workup

  1. temperaturethe reaction mixture was cooled to 0-5° C
  2. temperatureto warm to room temperature
  3. stirringstir for 2 h
  4. customThe solvents were evaporated under reduced pressure, dichloromethane
  5. additionwas added
  6. washthe mixture was washed with water
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-1adee2c1c1e04f8cb6fa1ec8d11c3520
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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