Potassium Carbonate → (S,S)-2-Methyl-5-(3-methyl-1,2,4-thiadiazol-5-yl)-2,5-diazabicyclo[2.2.1]heptane

HRID 2260806Notes

Reaction equation

HRID 2260806 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH3:7])[N:3]=1.[CH3:8][N:9]1[CH2:14][C@@H:13]2[CH2:15][C@H:10]1[CH2:11][NH:12]2.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(Cl)Cl>[CH3:8][N:9]1[CH2:14][C@@H:13]2[CH2:15][C@H:10]1[CH2:11][N:12]2[C:2]1[S:6][N:5]=[C:4]([CH3:7])[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11029795(1S,4S)-2-Methyl-2,5-diazabicyclo[2.2.1]heptaneHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazole

Product 1

HCID 57036075(S,S)-2-Methyl-5-(3-methyl-1,2,4-thiadiazol-5-yl)-2,5-diazabicyclo[2.2.1]heptaneYield 36.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.04 g of 5-chloro-3-methyl-1,2,4-thiadiazole, prepared by the procedure of J. Goerdeler, Chim. Ber., 1957, 90, 182, in 2 ml of tetrahydrofuran is added over one hour to a solution of 0.825 g of (S,S)-2-methyl-2,5-diazabicyclo[2.2.1]heptane and 0.77 g of potassium carbonate in 10 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature overnight, diluted with methylene chloride and the organic layer is washed with water. The methylene chloride solution is dried and concentrated in vacuo to dryness. The residue is purified by chromatography (aluminum oxide, Activity Grade 2.5: 2% methyl alcohol/methylene chloride) to give 0.56 g of the desired product:

Workup

  1. washthe organic layer is washed with water
  2. dry with materialThe methylene chloride solution is dried
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue is purified by chromatography (aluminum oxide, Activity Grade 2.5: 2% methyl alcohol/methylene chloride)

Sources & evidence

ORD record
ord-8cf852a12857412ebe9b93cbfd6a1649
Source dataset
uspto-grants-1995_12
Patent number
US05478939

Reaction notes

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