Tetrabutylammonium Fluoride → HCID 18395059, compound

HRID 863340Notes

Reaction equation

HRID 863340 reaction equation
C[Si](C)(C)[O:3][CH:4]1[CH2:12][CH2:11][CH2:10][C@@:9]2([CH3:13])[CH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:14]([CH3:29])[CH2:15][CH2:16][CH2:17][C@@:18]1([CH3:28])[O:22][C@H:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][C:19]1=[O:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:3][CH:4]1[CH2:12][CH2:11][CH2:10][C@@:9]2([CH3:13])[CH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:14]([CH3:29])[CH2:15][CH2:16][CH2:17][C@@:18]1([CH3:28])[O:22][C@H:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][C:19]1=[O:27]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57097194HCID 57097194, compound

Product 1

HCID 18395059HCID 18395059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 913 mg amount of (5R,2S)-5-{(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]pentyl}-5-methyl-2-t-butyl-1,3-dioxolan-4-one was placed in a 100 ml eggplant-shaped flask and dissolved in 10 ml of tetrahydrofuran. A tetrahydrofuran solution (1 M, 2.5 ml) of tetrabutylammonium fluoride was added under ice cooling, then the solution was stirred at the same temperature for 15 minutes, was returned to room temperature, then was stirred for 1 hour. Thereafter, 100 ml of ether and 20 ml of water for separation were added, extraction was performed from the aqueous layer by ether, then the organic layer was washed with saline and then was dried over anhydrous magnesium sulfate. Further, this was concentrated, then purified by a silica column (hexane/ethyl acetate=9/1 to 6/1) to obtain (5R,2S)-5-{(4R)-4-[(1R,7aR)-octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl]pentyl}-5-methyl-2-t-butyl-1,3-dioxolan-4-one in an amount of 764 mg (99%).

Workup

  1. customwas returned to room temperature
  2. stirringwas stirred for 1 hour
  3. customThereafter, 100 ml of ether and 20 ml of water for separation
  4. additionwere added
  5. extractionextraction
  6. washthe organic layer was washed with saline
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationFurther, this was concentrated
  9. custompurified by a silica column (hexane/ethyl acetate=9/1 to 6/1)

Sources & evidence

ORD record
ord-181988a4217b4653a0a6023685a49e0f
Source dataset
uspto-grants-1998_02
Patent number
US05719297

Reaction notes

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