Tetrabutylammonium Fluoride → HCID 89852684, compound

HRID 627289Notes

Reaction equation

HRID 627289 reaction equation
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[CH:7]=[C:8]([CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C)[C@H:9]2[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[CH:7]=[C:8]([CH2:23][CH2:24][OH:25])[C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89852507HCID 89852507, compound2×

Product 1

HCID 89852684HCID 89852684, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-6-(allyloxy)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 285, 0.96 g, 1.99 mmol) in THF (6 mL) at 0° C. was added tetrabutylammonium fluoride (1M in THF) (5.97 mL, 5.97 mmol). The reaction mixture was stirred for ˜1 hour and then concentrated onto silica gel. Silica gel chromatography (0%-10% methanol/dichloromethane) afforded the title compound (0.446 g, 88%) as a cloudy yellow oil.

Workup

  1. concentrationconcentrated onto silica gel

Sources & evidence

ORD record
ord-dc4471b559c34feba0e144a781889eb5
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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