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

HRID 330980Notes

Reaction equation

HRID 330980 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-0c86aa7825bf4cb9bc40e89065fb2c52
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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