HCID 131734466, compound → HCID 131734465, compound

HRID 589506Notes

Reaction equation

HRID 589506 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][C:9]=1[B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([SiH2:5][O:6][C:7]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:8]1[C:9]([B:17]2[O:18][C:19]([CH3:24])([CH3:25])[C:20]([CH3:23])([CH3:22])[O:21]2)=[CH:10][CH:11]=[CH:12][C:13]=1[NH2:14])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 131734466HCID 131734466, compound

Product 1

HCID 131734465HCID 131734465, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The nitro compound Intermediate 26 (10.0 g, 19.32 mmol) was dissolved in 300 ml EtOAc and Pd/C 10% (Pd) (2.0 g) were added. The mixture was hydrogenated at room temperature and normal pressure for 20 hours. The mixture was filtered over Kieselgur (Supelco) and evaporated. The residue was purified by flash chromatography on silica (cyclohexane to cyclohexane/EtOAc 4:1) to afford the compound Intermediate 27 as a yellow oil.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered over Kieselgur (Supelco)
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica (cyclohexane to cyclohexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-3665332486e040c7af3036422e80bcbb
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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