1-Methyl-3-pyrrolidinol → 3-Butoxy-4-(1-methyl-pyrrolidin-3-yloxy)-[1,2,5]thiadiazole

HRID 1377584Notes

Reaction equation

HRID 1377584 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]1.C([Li])CCC.[CH2:13]([O:17][C:18]1[C:22](S(C)(=O)=O)=[N:21][S:20][N:19]=1)[CH2:14][CH2:15][CH3:16]>C1COCC1.CCCCCC>[CH2:13]([O:17][C:18]1[C:22]([O:7][CH:4]2[CH2:5][CH2:6][N:2]([CH3:1])[CH2:3]2)=[N:21][S:20][N:19]=1)[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 930741-Methyl-3-pyrrolidinolHCID 196003073-Butyloxy-4-methanesulfonyl-1,2,5-thiadiazoleHCID 178418339Butyllithium

Product 1

HCID 108250553-Butoxy-4-(1-methyl-pyrrolidin-3-yloxy)-[1,2,5]thiadiazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-methyl-3-pyrrolidinol (0.6 g, 0.0059 mol) in THF (20 mL) was treated with 1.6M n-butyllithium in hexane (3.1 mL), 0.005 mol). To the solution was added 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1.0 g, 0.0042 mol) and the reaction heated to reflux overnight. The solvent was evaporated, the residue acidified with cold 1N HCl, and the mixture extracted with ether. The aqueous fraction was made basic, extracted with EtOAc, and the extracts washed with water. The extracts were dried and the solvent evaporated to give a liquid. The HCl salt (0.7 g) crystallized from EtOAc, m.p. 157°-158° C. (Compound 28).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. extractionthe mixture extracted with ether
  5. extractionextracted with EtOAc
  6. washthe extracts washed with water
  7. customThe extracts were dried
  8. customthe solvent evaporated
  9. customto give a liquid
  10. customThe HCl salt (0.7 g) crystallized from EtOAc, m.p. 157°-158° C. (Compound 28)

Sources & evidence

ORD record
ord-08a06b8ecaba442d9c84ce1970d23b91
Source dataset
uspto-grants-1997_09
Patent number
US05665745

Reaction notes

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