Allyl bromide → N-allyl-N-phenethylcarbamic acid tert-butyl ester

HRID 356860Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].[CH2:21](Br)[CH:22]=[CH2:23].[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:23][CH:22]=[CH2:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound.

Workup

temperatureCool again to 0° C. in an ice-bath
temperatureto reflux for 18 hours
temperatureCool to ambient temperature
extractionextract with ethyl acetate
dry with materialDry the organic layer over MgSO4
filtrationfilter
customevaporate in vacuo
washChromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

Sources & evidence

ORD record: ord-b2367990fe4f489bb4930b221cd94d7f
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840726

Reaction notes

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