HCID 118023500, compound → HCID 118022937, compound

HRID 522674Notes

Reaction equation

HRID 522674 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH2:4][O:3]1.[H][H]>[Pd].CO>[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 118023500HCID 118023500, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118022937HCID 118022937, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-2,2-dimethyl-4-(4-nitrophenyl)-1,3-dioxolane (3.6 g, 16.1 mmol) and 5% palladium on carbon (50% wet, 700 mg) in methanol (30 mL) was stirred under 1 atm hydrogen atmosphere (H2 balloon) at RT for 16 h. After the reaction mixture was filtered through a pad of Celite, the filtrate was concentrated to afford the title compound (3.1 g, 100%) as a yellow solid. MS (ES+) C11H15NO2 requires: 193, found: 194 [M+H]+.

Workup

  1. filtrationAfter the reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c7c00e4e3ce4a3f9115ddb2833977d3
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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