Dichloromethane → Di-tert-butyl 4-(aminooxy)pyrazolidine-1,2-dicarboxylate

HRID 2400683Notes

Reaction equation

HRID 2400683 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH:13]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:15]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14]1.C(Cl)Cl.O.NN>C(O)C>[NH2:3][O:12][CH:13]1[CH2:14][N:15]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 86694006di-tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrazolidine-1,2-dicarboxylate

Product 1

HCID 86694007Di-tert-butyl 4-(aminooxy)pyrazolidine-1,2-dicarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of di-tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrazolidine-1,2-dicarboxylate 142 (1.81 g, 4.18 mmol) in a solution of DCM (20 mL) and ethanol (4 mL) was added hydrazine hydrate (0.240 mL, 4.18 mmol) at room temperature. The mixture was stirred at room temperature overnight, filtered and concentrated to provide a residue which was subjected to chromatography to give 143 (1.04 g, 83%) as a white foam.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto provide a residue which

Sources & evidence

ORD record
ord-2070a1ae5ede49efa39b91c4a9b5f4c3
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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