Allyl bromide → HCID 67490756, compound

HRID 1917414Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][N:13]([C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[C:12](=[O:23])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:24](Br)[CH:25]=[CH2:26].C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>O1CCCC1>[CH2:26]([C@H:11]1[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH2:14][N:13]([C@@H:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])[C:12]1=[O:23])[CH:25]=[CH2:24]

Participants

Conditions

Temperature: -5 °C

Procedure

(4S)-4-(tert-Butyldimethylsilyloxy)methyl-2-oxo-1-[(1R)-1-phenylethyl]pyrrolidine (333.5 g, 1.00 mol) and allyl bromide (90.9 mL, 1.05 mol) were dissolved in tetrahydrofuran (1.10 L). Lithium hexamethyldisilazide (1.0 M solution in tetrahydrofuran) (1.10 L, 1.10 mol) was added dropwise at −15° C., and the mixture was stirred at −5° C. for one hour. The reaction solution was extracted with a saturated ammonium chloride solution and ethyl acetate. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. Thereafter, the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=4:1→2:1) to give 327 g of the title compound as a colorless syrup.

Workup

extractionThe reaction solution was extracted with a saturated ammonium chloride solution and ethyl acetate
washThen, the organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThereafter, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-720548660d6944559c5022131f27c71d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618094B2

Reaction notes

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