Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate → methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate

HRID 20506Notes

Reaction equation

HRID 20506 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([CH3:30])[O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22]CC2C=CC=CC=2)[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][CH2:9][C@H:10]([CH3:30])[O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59127165Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate

Product 1

HCID 59346877methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoateYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate (1000 mg, 2.33 mmol) was dissolved in methanol (30 mL) and 10% palladium on charcoal (100 mg) added. The mixture was stirred at ambient temperature for 36 h, filtered, evaporated in vacuo and chromatographed, 0-100% ethyl acetate in isohexane, to give methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate (750 mg). The material was used without further purification.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. customchromatographed

Sources & evidence

ORD record
ord-99e21a99e6824ba1883407aae338c159
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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