Hydrazine → tert-Butyl 3-(hydrazinecarbonyl)pyrrolidine-1-carboxylate

HRID 383769Notes

Reaction equation

HRID 383769 reaction equation
C[C:2]1([C:14]([O-:16])=O)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[NH2:17][NH2:18]>C(O)C>[NH:17]([C:14]([CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)=[O:16])[NH2:18]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 713021051-Tert-butyl 3-methylpyrrolidine-1,3-dicarboxylate

Product 1

HCID 4621605tert-Butyl 3-(hydrazinecarbonyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-tert-butyl 3-methylpyrrolidine-1,3-dicarboxylate (1.00 equiv.) and hydrazine (excess of 50% aq. solution) in ethanol (0.2 M final conc.) is heated to reflux. After the reaction is deemed complete, the reaction mixture is cooled to rt and partially concentrated. The resulting mixture is diluted with EtOAc, and the resulting organics are washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound i-13a.

Workup

  1. concentrationpartially concentrated
  2. additionThe resulting mixture is diluted with EtOAc
  3. washthe resulting organics are washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8ae6410e69b4506a1f42e3668b7c4fb
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

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