Water → HCID 21942816, compound

HRID 2218195Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-(N-tert-butoxycarbonyl-N-isopropylamino)-ethanol (3.00 g, 14.8 mmol) and benzyl bromide (2.6 ml, 22.1 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a solution of 60% sodium hydride (885 mg, 22.1 mmol) in anhydrous tetrahydrofuran (20 ml) under ice-cooling, and the mixture was stirred at 60° C. for four hours. Water (100 ml) was added to the reaction mixture under ice-cooling, the temperature was returned to room temperature, and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine (100 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate=4/1) to give 1.30 g (30%) of the target compound.

Workup

temperaturecooling
temperaturecooling
customwas returned to room temperature
extractionthe whole was extracted with ethyl acetate (100 ml)
washThe organic layer was washed with saturated brine (100 ml)
customEthyl acetate was evaporated under reduced pressure
customthe obtained oily matter was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-278581a696414a82a5ad0c89708c6960
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410987B2

Reaction notes

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