Sodium Bicarbonate → HCID 57867354, compound

HRID 1516255Notes

Reaction equation

HRID 1516255 reaction equation
[Si]([O:18][CH2:19][C@@H:20]1[C:24]([CH3:26])([OH:25])[C@:23]([F:28])([CH3:27])[CH:22]([O:29][CH3:30])[O:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>>[F:28][C@@:23]1([CH3:27])[CH:22]([O:29][CH3:30])[O:21][C@H:20]([CH2:19][OH:18])[C:24]1([CH3:26])[OH:25]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68979583HCID 68979583, compound

Product 1

HCID 57867354HCID 57867354, compoundYield 99.4%

Procedure

To a solution of (2R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyl-tetrahydrofuran-3-ol (about 6.3 g, 14.5 mmol) in tetrahydrafuran (about 100 ml) at about 0° C. was added 1N tetra butyl ammonium fluoride solution (about 14.5 ml, 14.5 mmol) drop wise for about 10 minutes and stirred at room temperature for about 1.5 hours. Completion of the reaction monitored by thin-layer chromatography and neutralized with saturated sodium bicarbonate. Aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with water, brine and dried over sodium sulphate and concentrated under reduced pressure, purified by silica gel column chromatography using 50% ethyl acetate: hexane as eluent furnished the title compound (2.8 g) as a colorless liquid. Yield: 99%; 1H NMR (300 MHz, CDCl3): δ 4.84 (d, 1H, J=11.1 Hz), 4.11 (m, 1H), 3.88-3.87 (m, 2H), 3.46 (s, 3H), 3.35 (s, 1H), 2.05 (m, 1H), 1.40 (d, 3H, J=23.4 Hz), 1.27 (d, 3H, J=2.1 Hz); Mass: [M+Na]+: 217 (100%).

Workup

  1. extractionAqueous layer was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with water, brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1e488a4433440c08e1622b02a1e4400
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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