Triethylamine → HCID 59401705, compound

HRID 2388666Notes

Reaction equation

HRID 2388666 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7].C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([S:24](Cl)(=[O:26])=[O:25])=[C:19]([CH3:28])[CH:18]=1>ClCCl>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH3:28])[C:20]([S:24]([N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[CH2:6][OH:7])(=[O:25])=[O:26])=[C:21]([CH3:23])[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 640091L-ProlinolHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 59401705HCID 59401705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-pyrrolidin-2-ylmethanol (2.2 g, 8.54 mmol) in dichloro-methane (20 ml) was added triethylamine (2.9 ml, 21.36 mmol) and the mixture was cooled to 0° C. Then a solution of 4-methoxy-2,6-dimethyl-benzenesulfonyl chloride (2 g, 8.547 m.mole) in dichloromethane (10 ml) was added and the mixture was stirred at room temperature for 2 h. TLC showed complete consumption of the starting material. The reaction mixture was diluted in dichloromethane and was washed with water and brine. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography.

Workup

  1. customconsumption of the starting material
  2. additionThe reaction mixture was diluted in dichloromethane
  3. washwas washed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-adfbfc4b7b604d7eac9d2865a85bb60a
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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