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

HRID 627174Notes

Reaction equation

[Si]([O:8][CH2:9][C@@H:10]1[C:16]([CH3:17])=[CH:15][C@@H:14]2[CH2:18][N:11]1[C:12](=[O:23])[N:13]2[O:19][CH2:20][CH:21]=[CH2:22])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[OH:8][CH2:9][C@@H:10]1[C:16]([CH3:17])=[CH:15][C@@H:14]2[CH2:18][N:11]1[C:12](=[O:23])[N:13]2[O:19][CH2:20][CH:21]=[CH2:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 100-mL round-bottom flask, was placed tetrahydrofuran (30 mL), (2S,5R)-2-[[(tert-butyldimethylsilyl)oxy]methyl]-3-methyl-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 148, 3.2 g, 9.45 mmol, 1.00 equiv) and it was cooled to 0° C., then TBAF (14.2 mL 1N in THF, 1.50 equiv) was added dropwise. The resulting solution was stirred for 1 h at 0° C. in a water/ice bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:2). This resulted in 1.6 g (75%) of the title compound as a light yellow solid.

Workup

customInto a 100-mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-2aca031aa9344a46a4e1210c2f233765
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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