Tetrabutylammonium Fluoride → HCID 66762737, compound

HRID 573772Notes

Reaction equation

HRID 573772 reaction equation
[Si]([O:8][CH:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]([CH2:24][OH:25])=[C:11]([I:26])[C:10]1=2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:25][CH2:24][C:12]1[C:13]([CH:21]([CH3:23])[CH3:22])=[N:14][C:15]2[CH2:16][C:17]([CH3:19])([CH3:20])[CH2:18][C@H:9]([OH:8])[C:10]=2[C:11]=1[I:26]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66761376HCID 66761376, compound

Product 1

HCID 66762737HCID 66762737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.67 g (S)-(5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-ylmethanol in 50 ml tetrahydrofurane are added 6.8 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofurane. The solution is stirred for 2 hours at room temperature, then the solvent is evaporated in vacuo and the residue is redissolved in dichloromethane. After washing successively with water, saturated aqueous sodium bicarbonate and brine the organic phase is dried with sodium sulphate. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 3:1).

Workup

  1. customthe solvent is evaporated in vacuo
  2. dissolutionthe residue is redissolved in dichloromethane
  3. washAfter washing successively with water, saturated aqueous sodium bicarbonate and brine the organic phase
  4. dry with materialis dried with sodium sulphate
  5. customThe solvents are evaporated in vacuo
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 3:1)

Sources & evidence

ORD record
ord-79da826b82804d3ebde8252f30189c9b
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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