Methyl 2-(5,5-dimethyl-5'-nitro-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate → Methyl 2-(5'-amino-5,5-dimethyl-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

HRID 571227Notes

Reaction equation

HRID 571227 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:24][O:23][C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=3)[N:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:6]2=[O:22])[O:4][CH2:3]1>CO.CCOC(C)=O.[Pd]>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:6](=[O:22])[C:5]12[O:23][CH2:24][C:2]([CH3:25])([CH3:1])[CH2:3][O:4]1

Participants

4

Reactant 1

HCID 86681647Methyl 2-(5,5-dimethyl-5'-nitro-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

Product 1

HCID 86681648Methyl 2-(5'-amino-5,5-dimethyl-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of methyl 2-(5,5-dimethyl-5′-nitro-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (344 mg, 0.982 mmol) and 10% w/w Pd/C (cat. amount) in MeOH/EtOAc 1:1 (50 ml) was hydrogenated at 15 psi in a Parr apparatus for 2 hours. The catalyst was removed by filtration, and the residue was evaporated affording crude methyl 2-(5′-amino-5,5-dimethyl-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (307 mg, 0.958 mmol, 98% yield) that was used in the following step without further purification. MS/ESI+ 321.0 [MH]+

Workup

  1. customThe catalyst was removed by filtration
  2. customthe residue was evaporated

Sources & evidence

ORD record
ord-ae19a3bd8d744eb7a87fc7d0f1f52686
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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