HCID 131730736, compound → HCID 131730737, compound

HRID 455996Notes

Reaction equation

HRID 455996 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:33])([CH3:32])[C:8]12[O:15][C:12]([C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH:13]=[CH:14]1)[CH2:11][C:10]([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)=[CH:9]2)([CH3:4])([CH3:3])[CH3:2]>CO.[Rh]>[C:19]([SiH2:18][O:17][C:16]([CH3:24])([CH3:23])[C:12]12[O:15][C:8]([C:7]([CH3:32])([CH3:33])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])([CH2:14][CH2:13]1)[CH2:9][C:10]([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)=[CH:11]2)([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 131730736HCID 131730736, compound

Product 1

HCID 131730737HCID 131730737, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[1,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]octa-2,6-dien-3-yl]-phenylamine (as prepared in the previous step, 500 mg, 1.03 mmol) and 5% Rh/Al2O3 (250 mg, 50 wt %) in 20 mL of MeOH was stirred at RT under H2 (balloon pressure) for 2 h. The Rh catalyst was removed by filtration on Celite, and the filtrate was concentrated in vacuo to give 500 mg of the 4-[1,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-2-en-3-yl]-phenylamine as a light brown oil Mass spectrum (ESI, m/z): Calcd. for C27H47NO3Si2, 490.3 (M+H), found 490.1.

Workup

  1. customThe Rh catalyst was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8da36607ab2e4e1dbc26d54f8c75bad0
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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