Dichloromethane → Di-tert-butyl{[4-(aminooxy)piperidin-1-yl]methylylidene}biscarbamate

HRID 2400637Notes

Reaction equation

HRID 2400637 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([N:17]1[CH2:22][CH2:21][CH:20]([O:23][N:24]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:19][CH2:18]1)=[N:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.O.NN>C(O)C>[C:12]([O:11][C:10](=[O:16])[NH:9][C:8]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][NH2:24])[CH2:21][CH2:22]1)=[N:7][C:6](=[O:35])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 86699594Di-tert-butyl [{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidin-1-yl}methylylidene]biscarbamate

Product 1

HCID 86699595Di-tert-butyl{[4-(aminooxy)piperidin-1-yl]methylylidene}biscarbamateYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture di-tert-butyl[{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidin-1-yl}methylylidene]biscarbamate 64 (2.30 g, 4.71 mmol) in a solution of DCM (40 mL) and ethanol (6 mL) was added hydrazine hydrate (0.270 mL, 4.71 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 65 (0.72 g, 43%) as a white foam.

Workup

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

Sources & evidence

ORD record
ord-cb0432e0401e4166a93620eb3221575c
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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