HCID 15491199, compound → HCID 15491200, compound

HRID 1954694Notes

Reaction equation

HRID 1954694 reaction equation
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:9](=O)[CH2:10][CH2:11][C:12]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:30]1([CH2:29][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10][CH2:11][C:12]([C:21]2[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=2)([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH3:13])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 15491199HCID 15491199, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15491200HCID 15491200, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the product from Example 7 (1.00 g, 2.15 mmol) in 25 mL of anhydrous tetrahydrofuran (THF) was treated dropwise with lithium aluminum hydride solution (4.3 mL of a 1M solution in THF). The resulting solution was heated at reflux for 18 hours. The reaction was cooled and quenched by the addition of saturated NH4Cl solution and extracted with THF. The combined organic extracts were washed with saturated NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated to give the title compound (1.03 g, 100%) as a white foam.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. customquenched by the addition of saturated NH4Cl solution
  5. extractionextracted with THF
  6. washThe combined organic extracts were washed with saturated NaCl solution
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4089af0557c847b5ba4352ba3ca14c75
Source dataset
uspto-grants-2000_09
Patent number
US06124280

Reaction notes

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