Triethylamine → HCID 15086802, compound

HRID 1534558Notes

Reaction equation

HRID 1534558 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][C:4]#[C:5][CH2:6][N:7]1[CH2:11][CH2:10][C@@H:9]([OH:12])[C:8]1=[O:13].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:14][N:2]([CH3:1])[CH2:3][C:4]#[C:5][CH2:6][N:7]1[CH2:11][CH2:10][C@@H:9]([O:12][S:23]([CH3:22])(=[O:25])=[O:24])[C:8]1=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 15086778HCID 15086778, compound

Product 1

HCID 15086802HCID 15086802, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.4 g of (R)-1-[4-(dimethylamino)-2-butynyl]-3-hydroxy-2-pyrrolidinone, 0.6 ml of triethylamine and 0.3 ml of methane sulfonyl chloride in 10 ml of dichloromethane was stirred at 0° C. for 1 hour. Saturated aqueous sodium carbonate was added and the mixture separated. The aqueous portion was washed with dichloromethane. The organic layer and wash were combined, washed with sodium chloride solution, dried and evaporated. The residue was evaporated from 10 ml of toluene. The residual oil was purified by chromatography (silica gel), giving 0.4 g of (R)-1-[4-(dimethylamino)-2-butynyl]-3-[(methane sulfonyl)oxy]-2-pyrrolidinone as a colorless oil.

Workup

  1. customthe mixture separated
  2. washThe aqueous portion was washed with dichloromethane
  3. washThe organic layer and wash
  4. washwashed with sodium chloride solution
  5. customdried
  6. customevaporated
  7. customThe residue was evaporated from 10 ml of toluene
  8. customThe residual oil was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-9765b8ae5ac343818c9e3fb03e3937de
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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