4-Toluenesulfonyl chloride → (R)-(1-methyl-5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

HRID 70520Notes

Reaction equation

HRID 70520 reaction equation
C(N(CC)CC)C.Cl.CN(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[OH:24][CH2:25][C@@H:26]1[N:30]([CH3:31])[C:29](=[O:32])[CH2:28][CH2:27]1>C(Cl)(Cl)Cl.O>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:24][CH2:25][C@H:26]2[CH2:27][CH2:28][C:29](=[O:32])[N:30]2[CH3:31])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 14876040(5R)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinone

Product 1

HCID 86658003(R)-(1-methyl-5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Triethylamine (5.26 mL), trimethylamine hydrochloride (1.07 g) and 4-methylbenzenesulfonyl chloride (5.6 g) were sequentially added to a solution of (R)-5-(hydroxymethyl)-1-methylpyrrolidin-2-one (2.93 g, 48.3 g, described in J. Med. Chem., 34(3), 1991, 887-900) in chloroform (40 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure to give (R)-(1-methyl-5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate as a yellow amorphous (6.6 g).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-916bc9820e4147d890d4537f7f1063cc
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…