Potassium tert-butoxide → trans-4-benzyltetrahydro-2H-furo[3,4-b][1,4]oxazin-3(4H)-one

HRID 81166Notes

Reaction equation

[CH2:1]([N:8]([C@H:13]1[C@H:17]([OH:18])[CH2:16][O:15][CH2:14]1)[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>CC(O)(C)C>[CH2:1]([N:8]1[C:9](=[O:12])[CH2:10][O:18][C@@H:17]2[CH2:16][O:15][CH2:14][C@@H:13]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of trans-N-benzyl-2-chloro-N-(4-hydroxytetrahydrofuran-3-yl)acetamide (4.7 g, 17.4 mmol) in t-BuOH (40 mL) was added KOt-Bu (1.0 M in THF; 34.8 mL, 34.8 mmol) solution at 25° C. The reaction mixture was stirred at 25° C. for 2 hours and then the solvent was evaporated under reduced pressure. The residue was dissolved in water and extracted with EtOAc (100 mL). The organic extract was washed with brine (40 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford trans-4-benzyltetrahydro-2H-furo[3,4-b][1,4]oxazin-3(4H)-one. MS APCl calc'd for C13H15NO3 [M+H]+ 234. found 234.

Workup

customthe solvent was evaporated under reduced pressure
dissolutionThe residue was dissolved in water
extractionextracted with EtOAc (100 mL)
extractionThe organic extract
washwas washed with brine (40 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a7150dc860d6473587c5561b02fc8374
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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