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

HRID 627160Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 129, 1.64 g, 5.05 mmol) in THF (40 mL), tetrabutylammonium fluoride (6.06 ml, 6.06 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. The mixture was concentrated and purified by silica gel column (40 g, 50-100% Hex/EA) to give the desired product (1.03 g) as an yellow oil.

Workup

concentrationThe mixture was concentrated
custompurified by silica gel column (40 g, 50-100% Hex/EA)

Sources & evidence

ORD record: ord-8142ed1dcc6a45a089fbc71a9af96d94
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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