1-(Diphenylmethyl)azetidin-3-one → HCID 21029909, compound

HRID 1829179Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.[CH:11]([N:24]1[CH2:27][C:26](=[O:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[CH:11]([N:24]1[CH2:27][C:26]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])([OH:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Methoxyphenylmagnesium bromide (5.9 ml, 1M solution in tetrahydrofuran, 5.9 mmol) was added to a cooled (−78° C.) solution of 1-benzhydryl-azetidin-3-one (WO 9412181) (1 g, 4.2 mmol) in tetrahydrofuran (20 ml), and the reaction stirred at −78° C. for 15 minutes, then allowed to warm to room temperature over 30 minutes. The mixture was partitioned between water (100 ml) and ethyl acetate (100 ml), the layers separated, and the aqueus phase extracted with ethyl acetate (100 ml). The combined organic solutions were washed with brine (100 ml), dried (MgSO4) and evaporated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using pentane:ethyl acetate (50:50) as eluant to afford the title compound as a white foam.

Workup

temperatureto warm to room temperature over 30 minutes
customThe mixture was partitioned between water (100 ml) and ethyl acetate (100 ml)
customthe layers separated
extractionthe aqueus phase extracted with ethyl acetate (100 ml)
washThe combined organic solutions were washed with brine (100 ml)
dry with materialdried (MgSO4)
customevaporated under reduced pressure
customThe residual yellow oil was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-e85f71e37c384fa2b2f25e1eeff548e9
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060836B2

Reaction notes

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