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

HRID 344022Notes

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-53edee12b4dc46d8a7c175ac1003615f
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05864045

Reaction notes

Loading…