Cesium fluoride → HCID 117761396, compound

HRID 1474631Notes

Reaction equation

HRID 1474631 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]([O:13][C:14]3[C:15](=[O:19])[CH2:16][CH2:17][CH:18]=3)=[CH:11][CH:10]=2)O1.[F-].[Cs+].[C:25]([O:28][C@H:29]1[C@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@:33]2([C:45]3[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([CH2:52]Br)[CH:46]=3)[O:44][C@@:30]1([CH2:54][O:55][C:56](=[O:58])[CH3:57])[CH2:31][O:32]2)(=[O:27])[CH3:26]>O1CCOCC1.C(OC(=O)C)C>[C:25]([O:28][C@H:29]1[C@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@:33]2([C:45]3[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([CH2:52][C:9]4[CH:10]=[CH:11][C:12]([O:13][C:14]5[C:15](=[O:19])[CH2:16][CH2:17][CH:18]=5)=[CH:20][CH:21]=4)[CH:46]=3)[O:44][C@@:30]1([CH2:54][O:55][C:56](=[O:58])[CH3:57])[CH2:31][O:32]2)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 86729345HCID 86729345, compound2×HCID 89444988HCID 89444988, compound

Product 1

HCID 117761396HCID 117761396, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)cyclopent-2-enone (295 mg, 0.989 mmol), CsF (296 mg, 1.95 mmol) in dioxane (3.1 mL), (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(bromomethyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (369.4 mg, 0.65 mmol, Intermediate 2) and Pd(PPh3) (60 mg, 0.05 mmol) were added under N2 atmosphere. The reaction mixture was heated to 110° C. for 1 h. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL), washed with water (20 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 2:8 Acetone:hexane) to provide title compound (150 mg, 35%) as off-white solid.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water (20 mL) and brine (20 mL) successively
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 2:8 Acetone:hexane)

Sources & evidence

ORD record
ord-43790542ad5c4e36a59861ee3d1a58d6
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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