Tetrabutylammonium Fluoride → (2S,5R)-2-(hydroxymethyl)-4-methyl-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one

HRID 627080Notes

Reaction equation

[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:23])=[CH:8][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[C:7]([CH3:23])=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 13, 1.76 g, 5.20 mmol) in THF (20 mL) at 0° C. was added tetrabutylammonium fluoride (1M in THF) (6.76 mL, 6.76 mmol). Stirred at 0° C. for 1 hour. The reaction mixture was concentrated onto silica gel. Silica gel chromatography (50%-100% ethyl acetate/hexanes) afforded the desired product (1.070 g, 92%) as a colorless oil.

Workup

concentrationThe reaction mixture was concentrated onto silica gel

Sources & evidence

ORD record: ord-e9e22af57c46413dbbe43e3759092d28
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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