Allyl bromide → HCID 12140790, compound

HRID 2414684Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:16][CH:17]=[CH2:18])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:29](Br)[CH:30]=[CH2:31]>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:16][CH:17]=[CH2:18])[CH2:9][CH:10]([CH2:31][CH:30]=[CH2:29])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl N-(tert-butoxycarbonyl)-3-(2-propenylamino)propionate (1.12 g, 4.86 mmol) was added 1N solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (THF) (5.8 mL) and allyl bromide (1.46 mL, 17.0 mmol) successively at −78° C. The mixture was stirred at 0° C. for an hour, then quenched by a saturated aqueous NH4Cl solution and extracted with ethyl acetate. The extract was washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:20) to give ethyl N-(tert-butoxycarbonyl)-2-(2-propenyl)-3-(2-propenylamino)propionate (0.7 g, 2.35 mmol, 48.4%) as a colourless oil.

Workup

customquenched by a saturated aqueous NH4Cl solution
extractionextracted with ethyl acetate
washThe extract was washed with water and brine
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe residue was purified by a silica gel column chromatography
washeluting with a mixture of ethyl acetate and n-hexane (1:20)

Sources & evidence

ORD record: ord-bef641a180f747e1b8b362b51294e93d
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812235B2

Reaction notes

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