HCID 66975384, compound → HCID 66975729, compound

HRID 1022597Notes

Reaction equation

HRID 1022597 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:14]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]2)[CH2:10][N+:11]([O-])=O)[CH:5]=[CH:6][C:7]=1[Cl:8]>C(O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:14]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]2)[CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 66975384HCID 66975384, compound

Product 1

HCID 66975729HCID 66975729, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of (4SR)-4-[(1RS)-1-(3,4-dichlorophenyl)-2-nitroethyl]-2,2-dimethyl-1,3-dioxolane (12.16 g) and Raney-nickel (10 g) in ethanol (100 ml) was stirred under a hydrogen atmosphere at room temperature for 5 hr. The reaction mixture was filtered through celite, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (3.40 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent of the filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-daf56d11f2a3419a8aab586702ef6ab1
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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