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

HRID 1053352Notes

Reaction equation

HRID 1053352 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:14]1.C(Cl)Cl.O.NN>C(O)C>[NH2:3][O:12][CH:13]1[CH2:14][CH2:15][N:16]([C:19]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:17][CH2:18]1

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-053ccdb0a02e4875b107b9fc513e668b
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

Loading…