Methyl iodide → tert-Butyl alpha-Methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

HRID 727523Notes

Reaction equation

[Li+].[CH3:2]C([N-]C(C)C)C.[CH3:9][CH:10]([CH3:34])[CH2:11][C:12]1([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25].IC>C1COCC1>[CH3:2][CH:26]([C:12]1([CH2:11][CH:10]([CH3:34])[CH3:9])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1=[O:25])[C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

LDA (1.5 mL, 3.0 mmol, 2.0M in heptane/THF/ethylbenzene) is added to a solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (967 mg, 2.69 mmol) and THF (11.0 mL) at -78° C. The solution is stirred at -78° C. for 30 minutes and then iodomethane (0.19 mL, 3.1 mmol) is added. The solution is stirred at -78° C. for 2 hours and then allowed to slowly warm to room temperature overnight. Aqueous workup (EtOAc, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc) gives 791 mg (79%) of the title compound as an oil.

Workup

stirringThe solution is stirred at -78° C. for 2 hours
temperatureto slowly warm to room temperature overnight
customAqueous workup (EtOAc, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record: ord-7520aad198d74a8481e2cf8c2f91e016
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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