Hydrazine hydrate (1:1) → (2S,3S)-2-Benzyl-3-Hydroxybutanohydrazide

HRID 2186507Notes

Reaction equation

HRID 2186507 reaction equation
[CH2:1]([C@@H:8]([C@@H:13]([OH:15])[CH3:14])[C:9](OC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:17][NH2:18]>CC(O)C>[CH2:1]([C@@H:8]([C@@H:13]([OH:15])[CH3:14])[C:9]([NH:17][NH2:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57077827Methyl (2S,3S)-2-Benzyl-3-Hydroxybutyrate

Product 1

HCID 57159903(2S,3S)-2-Benzyl-3-HydroxybutanohydrazideYield 64.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 0.70 g (3.36 mmol) of methyl (2S,3S)-2-benzyl-3-hydroxybutyrate (optical purity: 96%e.e.; anti/syn=98/2) was dissolved in 1 ml of 2-propanol, and 0.34 g (6.72 mmol) of hydrazine monohydrate was added thereto dropwise at room temperature. After the addition, the mixture was refluxed for 8 hours, and then stirred overnight to obtain a concentrate. The obtained concentrate was crystallized by using a mixed solvent of ethyl acetate and hexane to give 0.45 g (64%) of the title compound. Melting point: 167.1° C. Optical purity: >99.9%e.e. anti/syn>99/1

Workup

  1. customdropwise at room temperature
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 8 hours
  4. customto obtain a concentrate
  5. concentrationThe obtained concentrate
  6. customwas crystallized

Sources & evidence

ORD record
ord-12a6ac11dd184ca5ba3c561a57b82af8
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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