Isobutyl iodide → 3-(2-Methylpropyl)pyrrolidin-2-one

HRID 727537Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.C[Si](C)(C)[N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].I[CH2:20][CH:21]([CH3:23])[CH3:22]>C1COCC1>[CH3:20][CH:21]([CH3:23])[CH2:22][CH:13]1[CH2:14][CH2:15][NH:11][C:12]1=[O:16]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of LDA (2.0M, 111 mL, 222 mmol) and THF (300 mL) is cooled to -78° C. and a solution of 1-trimethylsilyl-2-pyrrolidinone (29.4 g, 221 mmol) in THF (145 mL) is added. After stirring for 45 minutes at -78° C., the enolate solution is added via cannula over 1 hour to a solution of 1-iodo-2-methylpropane (42.7 g, 232 mmol) in THF (200 mL) at -78° C. The solution is allowed to warm slowly and stirred at room temperature overnight. The reaction is quenched by the addition of 50 mL of acetic acid. Aqueous workup (EtOAc, MgSO4) and purification by column chromatography (30→100% EtOAc/hexane) gives 12.8 g of the title compound as an oil.

Workup

temperatureto warm slowly
stirringstirred at room temperature overnight
customThe reaction is quenched by the addition of 50 mL of acetic acid
customAqueous workup (EtOAc, MgSO4) and purification by column chromatography (30→100% EtOAc/hexane)

Sources & evidence

ORD record: ord-5487c2c6c2834ee09d2a631091ed38c5
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

Loading…