Water → HCID 13752057, compound

HRID 1458577Notes

Reaction equation

HRID 1458577 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:14]2[N:18]=[C:17]([C:19](OC)=[O:20])[CH:16]=[N:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>O1CCCC1>[OH:20][CH2:19][C:17]1[CH:16]=[N:15][N:14]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14239692HCID 14239692, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13752057HCID 13752057, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminium hydride (1.04 ml, 1M in tetrahydrofuran, 1.04 mmol) was added dropwise to a stirred solution of methyl 2-(triphenylmethyl)-1, 2,3-triazole-4-carboxylate (from step (a), 500 mg, 1.38 mmol) in anhydrous tetrahydrofuran (30 ml) at 0° C. under nitrogen. The mixture was stirred for 1 hour at 0° C. and then water (2 ml), 15% aqueous sodium hydroxide (4 ml) and then more water (4 ml) were added. The resulting suspension was filtered through Arbocel filter aid and the filtrate was dried (MgSO4) and concentrated under reduced pressure. The residue was partitioned between dichloromethane (150 ml) and water (150 ml). The dichloromethane layer was washed with water (600 ml) and then dried (MgSO4) and concentrated under reduced pressure to leave the title compound as a white solid (401 mg, 85%).

Workup

  1. filtrationThe resulting suspension was filtered through Arbocel
  2. filtrationfilter aid
  3. dry with materialthe filtrate was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between dichloromethane (150 ml) and water (150 ml)
  6. washThe dichloromethane layer was washed with water (600 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a00dbd8f44e54891ad7d7b0c603448e6
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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