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

HRID 1852774Notes

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 APCI 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-653ea6278d3a4619afa1c3c6718c7cc5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962611B2

Reaction notes

Loading…