Allyl bromide → HCID 69683505, compound

HRID 394973Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3]C.[CH:6](NC(C)C)(C)[CH3:7].[C:13]([O:17][C:18]([N:20]1[CH2:28][CH2:27][CH:23]([C:24]([O-:26])=[O:25])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(Br)C=C.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH2:3]([CH:21]1[CH2:22][CH:23]([C:24]([O:26][CH2:6][CH3:7])=[O:25])[CH2:27][CH2:28][N:20]1[C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])[CH:2]=[CH2:1]

Participants

Conditions

Temperature: -70 °C

Procedure

70 cm3 of a solution of butyllithium in hexane (2.5M concentration) were added, with stirring and under an inert atmosphere, to 150 cm3 of tetrahydrofuran cooled to a temperature in the region of −70° C., followed by addition of 50 cm3 of tetrahydrofuran and 23 cm3 of diisopropylamine predissolved in 300 cm3 of tetrahydrofuran. After a further addition of 50 cm3 of tetrahydrofuran, the mixture was stirred for 15 minutes at about −70° C., followed by addition of 45.15 g of ethyl de 1-(tert-butyloxycarbonyl)isonipecotate predissolved in 400 cm3 of tetrahydrofuran, and finally 50 cm3 of this same solvent. After stirring the mixture for 1 hour at a temperature in the region of −70° C., 16.7 cm3 of allyl bromide predissolved in 150 cm3 of tetrahydrofuran were added and the mixture was then warmed to about 20° C. and stirred for 17 hours. The mixture was poured into 200 cm3 of saturated aqueous ammonium chloride solution and then extracted with about 2 liters of ethyl acetate.

Workup

additionwere added
temperaturethe mixture was then warmed to about 20° C.
stirringstirred for 17 hours
extractionextracted with about 2 liters of ethyl acetate

Sources & evidence

ORD record: ord-b0f96c1a03534100b9380ebc02df01d9
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603005B2

Reaction notes

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