Water → [(2R,3S)-1-(4-methoxybenzyl)-2-methyl-5-oxopyrrolidin-3-yl]methyl rac-methanesulfonate

HRID 595218Notes

Reaction equation

HRID 595218 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][CH:15]1[CH:19]([CH3:20])[N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:17](=[O:30])[CH2:16]1.O>C(Cl)Cl>[CH3:8][S:9]([O:13][CH2:14][C@H:15]1[CH2:16][C:17](=[O:30])[N:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C@@H:19]1[CH3:20])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118208939rac-(4R,5S)-4-(hydroxymethyl)-1-(4-methoxybenzyl)-5-methylpyrrolidin-2-one

Product 1

HCID 118208685[(2R,3S)-1-(4-methoxybenzyl)-2-methyl-5-oxopyrrolidin-3-yl]methyl rac-methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.47 g, 14.57 mmol) and methanesulfonyl chloride (1.25 g, 10.93 mmol) were added to a solution of rac-(4R,5S)-4-(hydroxymethyl)-1-(4-methoxybenzyl)-5-methylpyrrolidin-2-one (1.8 g, 7.29 mmol) in DCM (36 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour, and then water (70 mL) was added and the mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to afford [(2R,3S)-1-(4-methoxybenzyl)-2-methyl-5-oxopyrrolidin-3-yl]methyl rac-methanesulfonate. MS ESI calc'd. for C15H22NO5S [M+H]+ 328. found 328. 1H NMR (400 MHz, CDCl3): δ 7.17 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 4.96-4.91 (m, 1H), 4.10-4.05 (m, 2H), 3.91-3.86 (m, 1H), 3.81 (s, 3H), 3.36-3.30 (m, 1H), 2.92 (s, 3H), 2.76-2.68 (m, 1H), 2.39-2.29 (m, 1H), 2.27-2.20 (m, 1H), 1.24 (d, J=6.4 Hz, 3H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL×3)
  2. dry with materialThe combined organic layers were 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-4e5a3d75ef49447ea3276e7b8543b538
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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