HCID 11133098, compound → HCID 15816085, compound

HRID 388729Notes

Reaction equation

HRID 388729 reaction equation
[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]([O:21][CH2:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25])[CH3:20])(C(C)(C)C)(C)C>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[OH:26][C:24]([CH3:25])([CH3:27])[CH2:23][CH2:22][O:21][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)[CH3:20]

Participants

4

Reactant 1

HCID 11133098HCID 11133098, compound

Product 1

HCID 15816085HCID 15816085, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Conditions

Temperature
80 °C

Procedure

The compound of Example 8E (230 mg, 0.58 mmol) is dissolved in 8 mL of 1 N tetra-n-butylammonium fluoride in tetrahydrofuran and warmed overnight at 80° C. The reaction mixture is partitioned between ether 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 50% ethyl acetate in hexanes to isolate the titled compound (140 mg, 85%).

Workup

  1. customThe reaction mixture is partitioned between ether 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 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cefa2d2ca7074cf98b15b22cfee09738
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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