Dimethylphenylsilane → HCID 67178081, compound

HRID 885185Notes

Reaction equation

HRID 885185 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=[CH2:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][SiH:18]([CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Pt](=O)=O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][Si:18]([CH3:25])([CH3:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 13014DimethylphenylsilaneHCID 11020618tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 67178081HCID 67178081, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

(S)-2,2-Dimethyl-4-vinyl-oxazolidine-3-carboxylic acid tert-butyl ester (750 mg; CAS 133625-87-3) was dissolved in dimethylphenylsilane (25 ml), platinum(IV)-oxide (187 mg) was added and the mixture was stirred overnight at room temperature. The catalyst was filtered off and the filtrate was evaporated in vacuo. The crude product was purified by column chromatography (SiO2; heptane/ethyl acetate=4:1) to give (S)-4-[2-(dimethyl-phenyl-silanyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.14 g, 95%) as colourless oil, which was used directly for the next step.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe crude product was purified by column chromatography (SiO2; heptane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-81f48c3f5170471eb5bcaa7096355c14
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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