Hexane → (S)-3-Butyloxy-4-(1-methyl-2-pyrrolidinylmethoxy)-1,2,5-thiadiazole

HRID 264804

Reaction equation

HRID 264804 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].C([Li])CCC.CCCCCC.[CH2:20]([O:24][C:25]1[C:29](S(C)(=O)=O)=[N:28][S:27][N:26]=1)[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH2:20]([O:24][C:25]1[C:29]([O:8][CH2:7][C@@H:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[N:28][S:27][N:26]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 8058HexaneHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 196003073-Butyloxy-4-methanesulfonyl-1,2,5-thiadiazoleHCID 178418339Butyllithium

Product 1

HCID 54562067(S)-3-Butyloxy-4-(1-methyl-2-pyrrolidinylmethoxy)-1,2,5-thiadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-1-methyl-2-pyrrolidinemethanol (0.86, 0.0075 mol) in THF (20 mL) was treated with 1.6M n-butyllithium in hexane (4.7 mL, 0.0075 mol). To the solution was added 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1.2 g, 0.005 mol) and the reaction heated to reflux for 6.5 h. The solvent was evaporated, the residue acidified with cold 1N HCl, and the mixture extracted with ether. The aqueous was made basic and extracted with EtOAc. The extracts were washed with water, dried, and the solvent evaporated to give a liquid. The HCl salt (0.72 g) crystallized from EtOAc, m.p. 115°-116° C. (Compound 31).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 6.5 h
  3. customThe solvent was evaporated
  4. extractionthe mixture extracted with ether
  5. extractionextracted with EtOAc
  6. washThe extracts were washed with water
  7. customdried
  8. customthe solvent evaporated
  9. customto give a liquid
  10. customThe HCl salt (0.72 g) crystallized from EtOAc, m.p. 115°-116° C. (Compound 31)

Sources & evidence

ORD record
ord-710ed8b3c0d6416883409822a55f47ab
Source dataset
uspto-grants-1997_07
Patent number
US05646289

Linked notes

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