Hydrazine hydrate (1:1) → tert-Butyl 4-(aminooxy)piperidine-1-carboxylate

HRID 2066893Notes

Reaction equation

HRID 2066893 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][NH2:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 24729482tert-Butyl 4-(aminooxy)piperidine-1-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 69a (6.93 g, 20 mmol) in 40 mL of DCM was added hydrazine hydrate (2.91 mL, 60 mmol). The mixture was stirred at room temperature for 4 h, cooled in an ice bath for 30 minutes, then filtered. The solid was rinsed with 10 mL of DCM and the filtrate was evaporated. After cooling in the fridge, more solid precipitated and the oil was dissolved in 10 mL of DCM and filtered. The filtrate was evaporated to give 4.31 g (99% yield) of 69b.

Workup

  1. temperaturecooled in an ice bath for 30 minutes
  2. filtrationfiltered
  3. washThe solid was rinsed with 10 mL of DCM
  4. customthe filtrate was evaporated
  5. temperatureAfter cooling in the fridge, more solid
  6. customprecipitated
  7. dissolutionthe oil was dissolved in 10 mL of DCM
  8. filtrationfiltered
  9. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c8ea92e478fd4ceebdb18905f15288da
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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