Triethylamine → HCID 118208950, compound

HRID 595195Notes

Reaction equation

HRID 595195 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.[CH3:13][O:14][C:15]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:16]=1[CH2:17][N:18]1[CH2:22][CH:21]([CH2:23][OH:24])[CH2:20][C:19]1=[O:25]>ClCCl.O>[CH3:1][S:2]([O:24][CH2:23][CH:21]1[CH2:20][C:19](=[O:25])[N:18]([CH2:17][C:16]2[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:15]=2[O:14][CH3:13])[CH2:22]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 642085931-[(2,4-Dimethoxyphenyl)methyl]-4-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 118208950HCID 118208950, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

MsCl (3.3 g, 28 mmol) and Et3N (3.8 g, 38 mmol) were added to a mixture of 1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)pyrrolidin-2-one (5.0 g, 19 mmol) in dichloromethane (50 mL) at 0° C. The mixture was stirred at room temperature for 10 hours then diluted with water and extracted with EtOAc. The EtOAc layer was dried over sodium sulfate and concentrated under reduced pressure to afford [1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-3-yl]methyl methanesulfonate. 1H NMR (400 MHz, CDCl3) δ 7.13-7.15 (m, 1H), 6.43-6.45 (m, 2H), 4.41-4.42 (m, 2H), 4.09-4.14 (m, 2H), 3.79-3.82 (m, 6H), 3.36-3.42 (m, 1H), 3.12-3.19 (m, 1H), 2.98 (s, 3H), 2.62-2.75 (m, 2H), 2.21-2.25 (m, 1H). MS ESI calc'd. for C15H22NO6S [M+H]+ 344. found 344.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe EtOAc layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fca8800753974cf881b428dcd2b21216
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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