Water → HCID 59633945, compound

HRID 1615072Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=[C:4]([O:18][CH3:19])[CH:3]=1.C([Li])CCC.CCCCCC.[C:31]([N:38]1[CH2:41][C:40](=[O:42])[CH2:39]1)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].O>O1CCCC1>[CH2:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:5]2[CH:6]=[CH:7][C:2]([C:40]3([OH:42])[CH2:39][N:38]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:41]3)=[CH:3][C:4]=2[O:18][CH3:19])=[CH:11][CH:12]=1)[CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-bromo-1-(4-ethylbenzyloxy)-2-methoxybenzene (1.2 g) prepared in (1) in THF (6.0 mL) was added dropwise 1.6 N n-butyllithium/hexane (2.8 mL) at −78° C. under argon atmosphere. The mixture was stirred at −78° C. for 30 min. A solution of 1-Boc-azetidin-3-one (0.64 g) in THF (6.0 mL) was added dropwise over 10 min to the mixture at −78° C. The reaction mixture was allowed to warm to RT and then stirred for 14 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=3/1 to 1/1) to give the title compound (0.88 g, 57%).

Workup

temperatureto warm to RT
stirringstirred for 14 hr
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record: ord-13ad4f11d18d4a96a1b12c8273acc938
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765739B2

Reaction notes

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