HCID 57907619, compound → [(5S)-6,7-Dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-5-yl]methanol

HRID 887153Notes

Reaction equation

HRID 887153 reaction equation
C([O:20][CH2:21][C@H:22]1[N:26]2[N:27]=[CH:28][N:29]=[C:25]2[CH2:24][CH2:23]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>Cl.O1CCOCC1>[N:29]1[CH:28]=[N:27][N:26]2[C@H:22]([CH2:21][OH:20])[CH2:23][CH2:24][C:25]=12

Participants

4

Reactant 1

HCID 57907619HCID 57907619, compound

Product 1

HCID 57907586[(5S)-6,7-Dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-5-yl]methanolYield 50.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product form step B above, 0.27 g (0.71 mmol) of (5S)-5-[(trityloxy)methyl]-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole, was dissolved in 35 mL of a 4.0 M solution of hydrogen chloride in anhydrous 1,4-dioxane. The reaction mixture was stirred for 10 min, quenched with 20 mL of methanol, then evaporated to dryness in vacuo. The residue was purified by reverse phase HPLC (TMC Pro-Pac C18; 0-90% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to yield the title compound (0.050 g, 50%). LC-MS: m/z (ES) 140 (MH)+.

Workup

  1. customquenched with 20 mL of methanol
  2. customevaporated to dryness in vacuo
  3. customThe residue was purified by reverse phase HPLC (TMC Pro-Pac C18; 0-90% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)

Sources & evidence

ORD record
ord-cf54468cb5574b6fa641477da4736825
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

Loading…