HCID 131728284, compound → HCID 178455452, compound

HRID 502610Notes

Reaction equation

HRID 502610 reaction equation
C(OC([NH:11][C:12]([NH:33]C(OCC1C=CC=CC=1)=O)=[N:13][CH:14]([C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=O)C1C=CC=CC=1>CCO.[Pd]>[C:20]([Si:17]([CH3:19])([CH3:18])[O:16][CH2:15][CH:14]([NH:13][C:12]([NH2:33])=[NH:11])[C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 131728284HCID 131728284, compound

Product 1

HCID 178455452HCID 178455452, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N,N′-bis(benzyloxycarbonyl)-N″-[2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-ethyl]-guanidine (12.48 g, 19.8 mmol) in 100 mL EtOH was added 5% Pd/C (0.5 g). The mixture was stirred under H2 at 50 psi. After 2 hours the mixture was filtered through a pad of celite and concentrated in vacuo to give N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-ethyl]-guanidine (7.6 g, 106%) as a white foam: MS (M+H)=362.

Workup

  1. filtrationAfter 2 hours the mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edb7cded5e42497497896b5497b4429e
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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