Water → HCID 67431242, compound

HRID 1662721Notes

Reaction equation

[CH3:1][N:2]([CH3:18])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[H-].[Na+].[CH2:21](I)[CH:22]=[CH2:23].O>C1COCC1>[CH2:23]([O:10][C@H:8]1[CH2:7][N:6]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[C@H:5]([C:3]([N:2]([CH3:18])[CH3:1])=[O:4])[CH2:9]1)[CH:22]=[CH2:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 9.6 g of tert-butyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxypyrrolidine-1-carboxylate in THF (100 ml) was added 937 mg of NaH and the reaction mixture was stirred at 60° C. for one hour. After returning to room temperature, 12.5 g of allyl iodide was added to the reaction solution, and the reaction mixture was refluxed for one hour. To the reaction solution was added water and the resulting mixture was extracted with EtOAc, then was washed with saturated brine. The organic layer was dried over Na2SO4, then the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: CHCl3/MeOH=18/1 to 9/1; v/v) to obtain 6.70 g of the title compound (light brown oil).

Workup

customAfter returning to room temperature
temperaturethe reaction mixture was refluxed for one hour
extractionthe resulting mixture was extracted with EtOAc
washwas washed with saturated brine
dry with materialThe organic layer was dried over Na2SO4
customthe drying agent was separated by filtration
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: CHCl3/MeOH=18/1 to 9/1; v/v)

Sources & evidence

ORD record: ord-4d439f24c0ef4400a77a7194967c67f2
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

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