Water → 5-((4-fluorophenyl)(hydroxy)methyl)-N-hydroxy-N,2,2-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxamide

HRID 2061554Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl.[CH3:12][NH:13][OH:14].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([OH:39])[C:23]2[CH:28]=[N:27][C:26]([C:29]([O:31]C)=O)=[C:25]3[O:33][C:34]([CH3:38])([CH3:37])[O:35][CH2:36][C:24]=23)=[CH:18][CH:17]=1.O>O1CCCC1>[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([OH:39])[C:23]2[CH:28]=[N:27][C:26]([C:29]([N:13]([OH:14])[CH3:12])=[O:31])=[C:25]3[O:33][C:34]([CH3:38])([CH3:37])[O:35][CH2:36][C:24]=23)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 78 °C

Procedure

1.8 mL of lithium bis(trimethylsilyl)amide solution (1.809 mmol, 9 eq, 1M in tetrahydrofuran) was added to 0.041 g of N-methylhydroxylamine hydrochloride (0.249 mmol, 1.1 eq.) in 5.0 mL of tetrahydrofuran (−78° C.) and stirred for 10 min at 78° C. 0.070 g of methyl 5-((4-fluorophenyl)(hydroxy)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate solution (0.201 mmol, 1 eq.) in 3.0 mL of tetrahydrofuran was then added followed by stirring for 30 min at −78° C. Water was then added to the reaction mixture followed by extraction with ethyl acetate. The resulting organic phases were then combined and concentrated under reduced pressure yielding 0.01 g of crude product (14% yield) as a white solid.

Workup

stirringby stirring for 30 min at −78° C
extractionfollowed by extraction with ethyl acetate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c4129451255640999d93b058833e9a07
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283366B2

Reaction notes

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