Triethylamine → HCID 22020971, compound

HRID 1793307Notes

Reaction equation

HRID 1793307 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][CH:2]1[CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:11][CH2:10][CH:2]1[O:3][C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[O:1]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22020937(2H-[1,3]Dioxolo[4,5-b]pyridin-2-yl)methanol

Product 1

HCID 22020971HCID 22020971, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of intermediate (5) (0.018 mol) and triethyl amine (0.036 mol) in DCM (80 ml) was stirred and cooled with an ice-water bath. Methanesulfonyl chloride (0.027 mol) was added dropwise and the resulting reaction mixture was stirred for one hour while cooling on an ice-bath. The crude reaction mixture was washed with water and brine, then extracted. The separated organic layer was dried, filtered and the solvent was evaporated, yielding 4.2 g of (±)-1,3-dioxolo[4,5-b]pyridine-2-methanol methanesulfonate (ester) (intermediate 6).

Workup

  1. temperaturecooled with an ice-water bath
  2. customthe resulting reaction mixture
  3. temperaturewhile cooling on an ice-bath
  4. customThe crude reaction mixture
  5. washwas washed with water and brine
  6. extractionextracted
  7. customThe separated organic layer was dried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a094a34095174cc381d440ed23ac3e00
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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