Tetrabutylammonium Fluoride → HCID 16731667, compound

HRID 2307816Notes

Reaction equation

HRID 2307816 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]([C:18](C)(C)[O:19][SiH2]C(C)(C)C)[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]([CH2:18][OH:19])[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 137328571HCID 137328571, compound

Product 1

HCID 16731667HCID 16731667, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 273A (3.14 g, 6.8 mmol) in THF (40 mL) was added TBAF (7.14 mL, 7.14 mmol) at rt. The solution was stirred at rt for 1 h and was concentrated. The residual oil was purified by flash chromatography (40-80% EtOAc in hexane) to give the desired product (2.19 g, 93%). MS (DCI) m/z 347, 349 (M+1)+.

Workup

  1. concentrationwas concentrated
  2. customThe residual oil was purified by flash chromatography (40-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-2b10536f71d640f1a8e80e8ea837a9f3
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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