Tetrabutylammonium Fluoride → 1-(4-Tert-butylphenyl)-2,5-bis(4-ethynylphenyl)pyrrolidine

HRID 1470980Notes

Reaction equation

HRID 1470980 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[C:23][Si](C)(C)C)=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:28]2[CH:33]=[CH:32][C:31]([C:34]#[C:35][Si](C)(C)C)=[CH:30][CH:29]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:12]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[CH:35])=[CH:30][CH:29]=3)[CH2:13][CH2:14][CH:15]2[C:16]2[CH:17]=[CH:18][C:19]([C:22]#[CH:23])=[CH:20][CH:21]=2)=[CH:9][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 687942901-(4-Tert-butylphenyl)-2,5-bis(4-((trimethylsilyl)ethynyl)phenyl)pyrrolidine

Product 1

HCID 873266311-(4-Tert-butylphenyl)-2,5-bis(4-ethynylphenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Dissolved the product of Example 105A (322 mg, 0.588 mmol) in anhydrous THF (5 mL) under nitrogen, added 1M TBAF in THF (1.322 mL, 1.322 mmol), and stirred at 25° C. for 30 min. The reaction darkened immediately upon addition and remained a brown color throughout the reaction. Removed solvent by rotary evaporation, dissolved the residue in Et2O (50 mL), washed with H2O (2×25 mL) and brine (25 mL), dried the organic phase over anhydrous MgSO4, filtered, and concentrated by rotary evaporation to a light tan foam (289 mg). Purified by flash chromatography (silica gel, 3.8 cm×14 cm, 20% CH2Cl2/hexanes) to the title compound as a light yellow foam (176 mg, 74%) as a mixture of stereoisomers. MS (ESI+) m/z 404 (M+H)+.

Workup

  1. additionThe reaction darkened immediately upon addition
  2. customthroughout the reaction
  3. customRemoved solvent by rotary evaporation
  4. dissolutiondissolved the residue in Et2O (50 mL)
  5. washwashed with H2O (2×25 mL) and brine (25 mL)
  6. dry with materialdried the organic phase over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation to a light tan foam (289 mg)
  9. customPurified by flash chromatography (silica gel, 3.8 cm×14 cm, 20% CH2Cl2/hexanes) to the title compound as a light yellow foam (176 mg, 74%) as a mixture of stereoisomers

Sources & evidence

ORD record
ord-9569d624f3af4a5aa9adad699ab96ec4
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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