HCID 68943357, compound → HCID 68673533, compound

HRID 388734Notes

Reaction equation

HRID 388734 reaction equation
C([Si]([O:8][C@H:9]1[CH2:17][CH2:16][CH2:15][C@@:14]2([CH3:18])[C@H:10]1[CH2:11][CH2:12][C@@H:13]2[C@H:19]([CH3:31])[CH:20]([O:29][CH3:30])[CH2:21][C@@H:22]([CH3:28])[C:23]([O:26][CH3:27])([CH3:25])[CH3:24])(C)C)(C)(C)C>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:30][O:29][CH:20]([CH2:21][C@@H:22]([CH3:28])[C:23]([O:26][CH3:27])([CH3:25])[CH3:24])[C@H:19]([C@@H:13]1[C@:14]2([CH3:18])[C@H:10]([C@@H:9]([OH:8])[CH2:17][CH2:16][CH2:15]2)[CH2:11][CH2:12]1)[CH3:31]

Participants

4

Reactant 1

HCID 68943357HCID 68943357, compound

Product 1

HCID 68673533HCID 68673533, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Conditions

Temperature
80 °C

Procedure

The compound of Example 10G (42 mg, 0.093 mmol) was dissolved in 1.5 mL of 1 N tetra-n-butylammonium fluoride in tetrahydrofuran, and warmed overnight at 80° C. The reaction mixture was partitioned between ethyl acetate and water; the organic phase was washed with brine and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 0% to 25% ethyl acetate in hexanes to provide the titled compound (27 mg, 86%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  6. washeluting with a gradient of 0% to 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c2715e76842a486da28e028f0f1378b7
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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