HCID 58994475, compound → HCID 58994419, compound

HRID 1508151Notes

Reaction equation

HRID 1508151 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]([CH3:19])([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([Si:5]([CH3:20])([CH3:21])[O:6][CH2:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)([CH3:19])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58994475HCID 58994475, compound

Product 1

HCID 58994419HCID 58994419, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl-dimethyl-[2-methyl-2-(4-nitro-phenyl)-propoxy]-silane (as prepared in the previous step, 1.70 g, 5.49 mmol) and 10% Pd/C (850 mg, 50 wt %) in 30 mL of EtOAc was stirred at RT under H2 (balloon pressure) for 6 h. The Pd catalyst was removed by filtration on Celite and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (5-10% EtOAc/DCM) to give 1.43 g (93%) of the title compound as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C16H29NOSi, 280.2 (M+H). found 280.4.

Workup

  1. customThe Pd catalyst was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography on silica gel (5-10% EtOAc/DCM)

Sources & evidence

ORD record
ord-b0f728f411c74c8ba4112450d8d58fad
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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