9-Borabicyclo(3.3.1)nonane → Ethyl(2S)-2-ethoxy-3-[4-(2-hydroxyethyl)phenyl]propanoate

HRID 970030Notes

Reaction equation

HRID 970030 reaction equation
B1C2CCCC1CCC2.[CH2:10]([O:12][C@@H:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH2:27])=[CH:22][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:11].O.O.C[N+]([O-:34])(C)C>C1COCC1.CCOCC>[CH2:10]([O:12][C@@H:13]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][OH:34])=[CH:24][CH:25]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:11]

Participants

6

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 198430Trimethylamine oxide dihydrateHCID 69418759Ethyl(2S)-2-ethoxy-3-(4-vinylphenyl)propanoate

Product 1

HCID 69418205Ethyl(2S)-2-ethoxy-3-[4-(2-hydroxyethyl)phenyl]propanoateYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

9-BBN (3.0 mmol, 6 mL of a 0.5 M solution in hexanes) was added to a stirred solution of ethyl(2S)-2-ethoxy-3-(4-vinylphenyl)propanoate (0.37 g, 1.48 mmol) in dry THF under argon. The reaction mixture was stirred for 22 h under argon. Trimethylamine N-oxide dihydrate (0.60 g, 5.4 mmol) was added and the mixture was heated to reflux overnight and diluted with ether (50 mL). The organic layer was washed with brine (×3), dried (MgSO4), filtered, and evaporated. The crude product was purified by flash chromatography (silica, heptane/ethyl acetate 3:1) to give the title compound as an colorless oil (0.24 g, 62%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. washThe organic layer was washed with brine (×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (silica, heptane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-fbaf27d4bbad489bafbcd01e5ca17b24
Source dataset
uspto-grants-2007_12
Patent number
US07309720B2

Reaction notes

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