Methyl iodide → (5S)-5-(p-toluenesulphonylmethyl)-1-methyl-2-pyrrolidinone

HRID 454316Notes

Reaction equation

[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][C@H:11]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:18]([N-]C(C)C)(C)C.[Li+].CI>C1COCC1>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([CH2:10][C@H:11]2[N:15]([CH3:18])[C:14](=[O:16])[CH2:13][CH2:12]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -70 °C

Procedure

(5S)-5-(p-Toluenesulphonylmethyl)-2-pyrrolidinone (0.8 g, 3 mmol) was dissolved in dry THF and cooled to −70° C. Lithium diisopropylamide was slowly added and the reaction stirred for 20 minutes before addition of methyl iodide (2 ml, excess). The reaction was allowed to warm to ambient temperature for over 2 hours. The reaction was partitioned between ethyl acetate and water, the organic layer separated, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by flash chromatography eluting from methylene chloride to 5% methanol/95% methylene chloride and the product evaporated to give (5S)-5-(p-toluenesulphonyl-methyl)-1-methyl-2-pyrrolidinone (340 mg, 40%) as a brown oil.

Workup

temperatureto warm to ambient temperature for over 2 hours
customThe reaction was partitioned between ethyl acetate and water
customthe organic layer separated
dry with materialdried over MgSO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by flash chromatography
washeluting from methylene chloride to 5% methanol/95% methylene chloride
customthe product evaporated

Sources & evidence

ORD record: ord-1bee2935a2fb43a0abf794641a963d96
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492560B2

Reaction notes

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