[2-(5-Acetyl-3-phenoxymethyl-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester → 4-Methyl-2-phenoxymethyl-6,7-dihydro-pyrazolo[1,5-a]pyrazine

HRID 1773787Notes

Reaction equation

HRID 1773787 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[C:14]([C:15](=O)[CH3:16])=[CH:13][C:12]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:11]1)(C)(C)C>Cl.O1CCOCC1>[CH3:16][C:15]1[C:14]2[N:10]([N:11]=[C:12]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)[CH2:9][CH2:8][N:7]=1

Participants

4

Reactant 1

HCID 67958451[2-(5-Acetyl-3-phenoxymethyl-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 679598694-Methyl-2-phenoxymethyl-6,7-dihydro-pyrazolo[1,5-a]pyrazineYield 99.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

[2-(5-Acetyl-3-phenoxymethyl-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (0.2 g, 0.56 mmol) was dissolved in a 4M solution of HCl in 1,4-dioxane (2.12 mL) under nitrogen. The mixture was stirred at room temperature for 30 minutes and then the solvents evaporated in vacuo. The residue was basified with a saturated solution of Na2CO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 4-methyl-2-phenoxymethyl-6,7-dihydro-pyrazolo[1,5-a]pyrazine (135 mg, 99% yield) as a brown solid that was used without further purification.

Workup

  1. customthe solvents evaporated in vacuo
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-4aa2d27bf6894288b2b96ee75056f6a5
Source dataset
uspto-grants-2016_02
Patent number
US09255103B2

Reaction notes

Loading…