Hexane → HCID 67789227, compound

HRID 231234Notes

Reaction equation

[OH:1][CH:2]([C@H:4]1[C@H:7]([CH:8]=[CH2:9])[NH:6][C:5]1=[O:10])[CH3:3].C([Li])CCC.CCCCCC.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>O1CCCC1.C(O)(=O)C.O.C(OCC)(=O)C>[OH:1][CH:2]([C@H:4]1[C@H:7]([CH:8]=[CH2:9])[N:6]([Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:5]1=[O:10])[CH3:3]

Participants

Conditions

Temperature: -65 °C

Procedure

In an argon stream, a solution of trans-3-(1-hydroxyethyl)-4-vinyl-2-azetidinone (0.10 g) in dry tetrahydrofuran (10 ml) is cooled to -75° C. and a commercial n-butyllithium (1.6M)-hexane solution (0.9 ml) is added dropwise to the solution while maintaining a temperature at -65° C. or lower. The mixture is stirred at -75° C. for an hour and a solution of tert-butyldimethylsilyl chloride (0.16 g) in dry tetrahydrofuran (2 ml) is added dropwise at -70° C. or lower. The reaction mixture is further stirred at -73° C. for 0.5 hour and poured into a mixture of ethyl acetate (70 ml), water (50 ml) and acetic acid (2 ml). The organic layer is separated, adjusted to pH 7.0 with aqueous sodium hydrogen carbonate, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 0.1 g of trans-3-(1-hydroxyethyl)-1-(tert-butyldimethylsilyl)-4-vinyl- 2-azetidinone.

Workup

stirringThe reaction mixture is further stirred at -73° C. for 0.5 hour
customThe organic layer is separated
washwashed with aqueous sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-07c213e9f36a4e288613e490bb356a76
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845210

Reaction notes

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