Aluminium lithium hydride → HCID 68312729, compound

HRID 1530683Notes

Reaction equation

HRID 1530683 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([O:18][C:19]1[CH:41]=[CH:40][C:22]2[C:23]3[N:27]([CH2:28][CH2:29][O:30][C:21]=2[CH:20]=1)[CH:26]=[C:25]([C:31]1[N:32]([CH:37]([CH3:39])[CH3:38])[N:33]=[C:34]([CH3:36])[N:35]=1)[N:24]=3)([CH3:17])[C:12](OCC)=[O:13])C>C1COCC1>[CH:37]([N:32]1[C:31]([C:25]2[N:24]=[C:23]3[N:27]([CH2:28][CH2:29][O:30][C:21]4[CH:20]=[C:19]([O:18][C:11]([CH3:17])([CH2:12][OH:13])[CH2:10][OH:9])[CH:41]=[CH:40][C:22]=43)[CH:26]=2)=[N:35][C:34]([CH3:36])=[N:33]1)([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68313075HCID 68313075, compound

Product 1

HCID 68312729HCID 68312729, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled suspension of LiAlH4 (34 mg, 0.892 mmol) in THF (3 mL) was added a solution of 2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylmalonic acid diethyl ester (148 mg, 0.297 mmol) in THF (2 mL). The ice bath was removed and stirring at RT was continued for 1.5 h. To the reaction mixture was added EtOAc (5 mL) and stirring was continued for 10 min. An aqueous solution of Rochelle's salt was then added and stirring continued for a further 30 min. The mixture was filtered through a Celite® pad and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-12% MeOH in DCM) affording the title compound (79.4 mg, 65%). LCMS (Method B): RT 2.32 min [M+H]+ 414.

Workup

  1. customThe ice bath was removed
  2. additionTo the reaction mixture was added EtOAc (5 mL)
  3. stirringstirring
  4. waitwas continued for 10 min
  5. additionAn aqueous solution of Rochelle's salt was then added
  6. stirringstirring
  7. waitcontinued for a further 30 min
  8. filtrationThe mixture was filtered through a Celite® pad
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washThe combined organic phases were washed with brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo
  13. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-12% MeOH in DCM)

Sources & evidence

ORD record
ord-8a949e9899414a8fb4f4b2e9923020e8
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…