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

HRID 1053402Notes

Reaction equation

HRID 1053402 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-f47da5eed1d747629ac2334ead9bc11b
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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