HCID 9888784, compound → (R)-(-)-1-(3,4-di(t-butyldimethylsiloxy)phenyl)-2-aminoethanol

HRID 1271622Notes

Reaction equation

HRID 1271622 reaction equation
[O:1]([C:9]1[CH:10]=[C:11]([C@@H:23]([OH:28])[CH2:24][N+:25]([O-])=O)[CH:12]=[CH:13][C:14]=1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H][H]>CO.[Pd]>[O:1]([C:9]1[CH:10]=[C:11]([C@@H:23]([OH:28])[CH2:24][NH2:25])[CH:12]=[CH:13][C:14]=1[O:15][Si:16]([C:19]([CH3:21])([CH3:20])[CH3:22])([CH3:18])[CH3:17])[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 9888784HCID 9888784, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15313692(R)-(-)-1-(3,4-di(t-butyldimethylsiloxy)phenyl)-2-aminoethanolYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

100 mg of optically active 1-(3,4-di(t-butyldimethylsiloxy)phenyl)-2-nitroethanol obtained in example 1 was dissolved in 10 ml of methanol, and 10 mg of 10% Pd/C was added to the solution, after which the mixture was reacted at 20° C. under the hydrogen pressure of 0.1 MPa for 20 hours, so as to obtain 89.3 mg of the intended compound (in a yield of 96%, with an optical purity of 94% e.e.).

Sources & evidence

ORD record
ord-e16873283ad2432a87ace7d79e231644
Source dataset
uspto-grants-2007_04
Patent number
US07205425B2

Reaction notes

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