3-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one → HCID 59410188, compound

HRID 452245Notes

Reaction equation

HRID 452245 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[C:22](=[O:38])[N:23]([C:27]2[C:32]([CH3:33])=[CH:31][C:30]([N+:34]([O-])=O)=[CH:29][C:28]=2[CH3:37])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C1COCC1.[Pd]>[NH2:34][C:30]1[CH:31]=[C:32]([CH3:33])[C:27]([N:23]2[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:22]2=[O:38])=[C:28]([CH3:37])[CH:29]=1

Participants

5

Reactant 2

HCID 594101853-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 59410188HCID 59410188, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

970 mg (1.84 mmol) of the compound from Example 54A are dissolved in 20 ml of THF. 200 mg of palladium on carbon are then added, and the mixture is hydrogenated at RT in a hydrogen atmosphere under atmospheric pressure. The mixture is then filtered through kieselguhr, the filter cake is washed three times with THF and the filtrate is freed from the solvent. The reaction product (1.00 g) is reacted further without further purification.

Workup

  1. filtrationThe mixture is then filtered through kieselguhr
  2. washthe filter cake is washed three times with THF
  3. customThe reaction product (1.00 g) is reacted further without further purification

Sources & evidence

ORD record
ord-ae73cee7ef4b4fd2b157267bb0f8b500
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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