Tetrahydrofuran → HCID 67974700, compound

HRID 2046196Notes

Reaction equation

HRID 2046196 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]([CH3:27])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]2[N:15]=[C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[C:11]2[C:10]1=[O:26])(C)(C)C.C1COCC1>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:6][CH:7]([CH3:27])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]2[N:15]=[C:16]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:17]=[C:11]2[C:10]1=[O:26]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 70654271HCID 70654271, compound

Product 1

HCID 67974700HCID 67974700, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

(Rac)-5-[2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (70 mg, 0.13 mmol) was dissolved in a 1M solution of TBAF in THF (0.13 mL, 0.13 mmol). The mixture stirred at room temperature for 16 hours. Then the solvent was evaporated in vacuo to yield a yellow crude that was purified by flash column chromatography (silica; MeOH in DCM from 0/100 to 10/90) to yield (rac)-5-(2-hydroxy-propyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (20 mg, 51% yield) as a white solid.

Workup

  1. customThen the solvent was evaporated in vacuo
  2. customto yield a yellow crude that
  3. customwas purified by flash column chromatography (silica; MeOH in DCM from 0/100 to 10/90)

Sources & evidence

ORD record
ord-14cc64d5479142948c9aa7833c734482
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

Loading…