Triethylamine → [1-(2,4-Dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate

HRID 595214Notes

Reaction equation

HRID 595214 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:13][O:14][C:15]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:16]=1[CH2:17][N:18]1[CH2:22][C:21]([CH2:24][OH:25])([CH3:23])[CH2:20][C:19]1=[O:26]>C(Cl)Cl.O>[CH3:1][S:2]([O:25][CH2:24][C:21]1([CH3:23])[CH2:20][C:19](=[O:26])[N:18]([CH2:17][C:16]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:15]=2[O:14][CH3:13])[CH2:22]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1317345741-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-4-methylpyrrolidin-2-one

Product 1

HCID 118208667[1-(2,4-Dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (305 mg, 2.65 mmol) and triethylamine (540 mg, 5.35 mmol) were added to a solution of 1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-4-methylpyrrolidin-2-one (500 mg, 1.75 mmol) in DCM (5 mL) at 0° C. The mixture was stirred at room temperature for 16 hours and then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give [1-(2,4-dimethoxybenzyl)-3-methyl-5-oxopyrrolidin-3-yl]methyl methanesulfonate. MS ESI calc'd. for C16H24NO6S [M+H]+ 358. found 358. 1H NMR (400 MHz, CDCl3): δ 7.15 (d, J=8.4 Hz, 1H), 6.46-6.44 (m, 2H), 4.41 (s, 2H), 4.02-3.96 (m, 2H), 3.81 (s, 3H), 3.80 (s, 3H), 3.22 (d, J=6.4 Hz, 1H), 2.99-2.95 (m, 4H), 2.41 (d, J=16.8 Hz, 1H), 2.24 (d, J=16.8 Hz, 1H), 1.19 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-7b5441032e994be9a183dd67b045f3ac
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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