Hydrazine hydrate (1:1) → HCID 86698011, compound

HRID 518858Notes

Reaction equation

HRID 518858 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:25][CH2:24][C:12]3([N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:14][CH2:13]3)[CH2:11]2)=[CH:6][C:5]=1[O:26][CH:27]([CH3:29])[CH3:28])([O-])=O.O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:25][CH2:24][C:12]3([N:16]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:14][CH2:13]3)[CH2:11]2)=[CH:6][C:5]=1[O:26][CH:27]([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866980101,7-Diazaspiro[4.4]nonane-1-carboxylic acid, 7-[3-(1-methylethoxy)-4-nitrophenyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86698011HCID 86698011, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 400 mg of 2-methylpropan-2-yl 7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate, 592 mg of hydrazine hydrate and 52.5 mg of 10% palladium-on-carbon in 10 ml of ethanol is refluxed for 1 h. The mixture is filtered and the filtrate is concentrated under reduced pressure, so as to obtain 365 mg of 2-methylpropan-2-yl 7-[4-amino-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate in the form of a mauve gum.

Workup

  1. temperatureis refluxed for 1 h
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3fd5281d19b4f3fadf8061b5277b533
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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