HCID 137328991, compound → HCID 137328990, compound

HRID 1879496Notes

Reaction equation

HRID 1879496 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:20])([CH3:19])[C:8]1[CH:9]=[C:10]([CH2:17][OH:18])[CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:14][C:12]1[CH:11]=[C:10]([CH2:17][OH:18])[CH:9]=[C:8]([C:7]([CH3:20])([CH3:19])[O:6][SiH2:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH:13]=1

Participants

4

Reactant 1

HCID 137328991HCID 137328991, compound

Product 1

HCID 137328990HCID 137328990, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium-on-carbon (53 mg) was added to a magnetically stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-nitro-phenyl]-methanol (535 mg, 1.80 mmol) in ethanol (20 mL). The heterogeneous mixture was purged twice using vacuum and dry nitrogen, then stirred at room temperature under hydrogen at atmospheric pressure. After three hours, the reaction mixture was filtered through a pad of Celite®. The pad was washed with ethanol (2×20 mL) and the filtrate was concentrated to give crude [3-amino-5-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-methanol (515 mg) as an off-white solid, which was used directly in the next step without purification.

Workup

  1. customThe heterogeneous mixture was purged twice
  2. filtrationthe reaction mixture was filtered through a pad of Celite®
  3. washThe pad was washed with ethanol (2×20 mL)
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9db558be6a224ad09998e5c4263afbc4
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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