Triethylamine → HCID 118208498, compound

HRID 595193Notes

Reaction equation

HRID 595193 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.[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][CH:21]([CH:23]([OH:25])[CH3:24])[CH2:20][C:19]1=[O:26]>ClCCl.O>[CH3:1][S:2]([O:25][CH:23]([CH:21]1[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)[CH3:24])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118208785HCID 118208785, compound

Product 1

HCID 118208498HCID 118208498, 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-(1-hydroxyethyl)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-[1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-3-yl]ethyl methanesulfonate. 1H NMR (400 MHz, CDCl3) δ 7.10˜7.13 (m, 1H), 6.43-6.45 (m, 2H), 4.76-4.78 (m, 1H), 4.41-4.42 (m, 2H), 3.79-3.82 (m, 6H), 3.36-3.42 (m, 1H), 3.12-3.19 (m, 1H), 2.98 (s, 3H), 2.23-2.59 (m, 3H), 1.26-1.42 (d, J=7.2 Hz, 3H). MS ESI calc'd. for C16H24NO6S [M+H]+ 358. found 358.

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-9a67a8766b2e44a089c5c9d9ab4e2524
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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