Triethylamine → HCID 13306708, compound

HRID 572028Notes

Reaction equation

HRID 572028 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:1][CH2:2][C@@H:3]1[CH2:4][CH2:5][C:6](=[O:8])[NH:7]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 13306708HCID 13306708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative).

Workup

  1. customit was partitioned between water and dichloromethane (3×)
  2. dry with materialdried over Na2SO4
  3. customthe drying agent was removed by filtration
  4. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2f984cc3c8ed407b91d68c92ac6132ee
Source dataset
uspto-grants-2015_05
Patent number
US09029361B2

Reaction notes

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