HCID 66721612, compound → HCID 66721347, compound

HRID 1640155Notes

Reaction equation

HRID 1640155 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-])=O)[CH:10]=2)[CH2:4][O:3]1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=2)[NH2:19])[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 66721612HCID 66721612, compound

Product 1

HCID 66721347HCID 66721347, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4R)-2,2-dimethyl-4-{[3-nitro-5-(trifluoromethyl)phenoxy]methyl}-1,3-dioxolane (0.7770 g, 2.4 mmol) was dissolved in EtOAc (30 mL) and Pd (77 mg, 10% on carbon) was added. The reaction mixture was allowed to stir at rt under an atmosphere of hydrogen for 6 h. The reaction mixture was filtered through a pad of Celite and washed with EtOAc. The solvents were evaporated to give 3-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-5-(trifluoromethyl)-aniline (700 mg, 100%) as a white solid. LCMS: (FA) ES+291.9.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with EtOAc
  3. customThe solvents were evaporated

Sources & evidence

ORD record
ord-e60234c510054c7db4ad138b8cdf5581
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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