Imidazole → HCID 24886194, compound

HRID 1034576Notes

Reaction equation

HRID 1034576 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8](=[O:13])[CH2:9][C@@H:10]([OH:12])[CH:11]=1)=[O:5])[CH3:2].N1C=CN=C1.[CH2:19]([Si:21]([CH2:25][CH3:26])([CH2:23][CH3:24])Cl)[CH3:20]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8](=[O:13])[CH2:9][C@@H:10]([O:12][Si:21]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:19][CH3:20])[CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 58922286HCID 58922286, compound

Product 1

HCID 24886194HCID 24886194, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

25 g of (R)-2-ethoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one (5 g, 98% e.e.) was dissolved in ethyl acetate and the solution was placed in a nitrogen purged flask. Imidazole (13.87 g, 204 mmol) was added. The solution was cooled to 0° C. and triethylchlorosilane (26.6 g, 176 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for another 15 hours. After filtration, the filtrate was washed with a saturated sodium bicarbonate solution and a brine solution, respectively, dried over anhydrous magnesium sulfate, and concentrated to obtain the titled compound (38.5 g, 95%). [α]D: +27.8° (c 1.0, CH3CN).

Workup

  1. customthe solution was placed in a nitrogen purged flask
  2. temperatureto warm to room temperature
  3. filtrationAfter filtration
  4. washthe filtrate was washed with a saturated sodium bicarbonate solution
  5. dry with materiala brine solution, respectively, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5704aea6adf44920983cdeaf6cdffc44
Source dataset
uspto-grants-2013_10
Patent number
US08546114B2

Reaction notes

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