Acetonitrile → D-Tartrate

HRID 705685Notes

Reaction equation

HRID 705685 reaction equation
C[C:2]1[N:6]=[C:5](C2CCCNC2)[O:4][N:3]=1.[C:13]([OH:22])(=[O:21])[C@H:14]([C@@H:16]([C:18]([OH:20])=[O:19])[OH:17])[OH:15].C(#N)C>CO>[C:18]([C@H:16]([C@@H:14]([C:13]([O-:22])=[O:21])[OH:15])[OH:17])([O-:20])=[O:19].[O:4]1[CH:5]=[N:6][CH:2]=[N:3]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 439655D-Tartaric acidHCID 64866033-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine

Product 2

HCID 5460284D-TartrateHCID 64514631,2,4-Oxadiazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-5-(piperidin-3-yl)-1,2,4-oxadiazole (0.83 g, 0.0050 mol) and D-tartaric acid (0.74 g, 0.0050 mol) were dissolved in hot methanol (10 mL) and the solution was refluxed for 15 minutes. 30 mL of acetonitrile was added and the resulting solution was allowed to cool to room temperature. The crystals were filtered, washed with 10 mL of 1:3 methanol:acetonitrile, and recrystallized 3 times from methanol:acetonitrile (10 mL 20 mL) as before to give the D-tartrate salt of S-(+)-3-methyl-5-piperidin-3-yl)-1,2,4-oxadiazole (3a), 193 mg white solid. The optical purity 100% ee, as determined by HPLC analysis (Chiral Technologies Chiral-AGP, 4.0 mm×150 mm, 0.5% methanol 20 mM sodium phosphate pH=7). MS (ESI) m/z 168 [M+1]+. 1H NMR (DMSO-d6) δ 1.67-1.79 (m, 3H), 2.10-2.13 (m, 1H), 2.33 (s, 3H), 2.76-2.82 (t, 1H), 3.01-3.14 (m, 2H), 3.31-3.36 (m, 1H), 3.44-3.47 (m, 1H), 3.95 (s, 1H).

Workup

  1. temperaturethe solution was refluxed for 15 minutes
  2. filtrationThe crystals were filtered
  3. washwashed with 10 mL of 1:3 methanol
  4. customacetonitrile, and recrystallized 3 times from methanol

Sources & evidence

ORD record
ord-b2585300ad9a469f979538eb0cfc40e4
Source dataset
uspto-grants-2015_11
Patent number
US09174972B2

Reaction notes

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