HCID 90018303, compound → HCID 118151698, compound

HRID 1506956Notes

Reaction equation

HRID 1506956 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[O:12][C@@H:11]1[CH2:17][OH:18])([O-])=O>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:10]1[O:14][C:13]([CH3:15])([CH3:16])[O:12][C@@H:11]1[CH2:17][OH:18]

Participants

4

Reactant 1

HCID 90018303HCID 90018303, compound

Product 1

HCID 118151698HCID 118151698, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ((4R,5R)-5-(2-nitrophenyl)-2,2-dimethyl-1.3-dioxolane-4-yl)methanol (Preparation example 46, 14 g) in EtOAc was added Pd(OH)2 (20 wt %, 2.8 g) under hydrogen gas (balloon). The mixture was stirred for 6 h then the resulting mixture was filtered through celite and concentrated under reduced pressure. The crude product was purified by SiO2 gel column chromatography to give title compound (7.5 g 65˜85%)

Workup

  1. filtrationthe resulting mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by SiO2 gel column chromatography

Sources & evidence

ORD record
ord-68e7ecb2fddc43998b685d34237ae346
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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