Water → HCID 67410414, compound

HRID 714631Notes

Reaction equation

HRID 714631 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[N:9]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 53419305HCID 53419305, compound

Product 1

HCID 67410414HCID 67410414, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

80 mg (0.32 mmol) of the compound from Example 35A were dissolved in 2 ml of THF, and 335 μl (0.34 mmol) of a 1 N solution of lithium aluminum hydride in THF were added at −10° C. Over a period of one hour, the mixture was then warmed to RT. For work-up, 2 ml of water and 5 ml of saturated potassium sodium tartrate solution were added and the mixture was extracted twice with in each case 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave 61 mg (83% of theory) of the target compound in a purity of 91%.

Workup

  1. extractionthe mixture was extracted twice with in each case 10 ml of ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0309894cba8f4d73845bb9e410caf3df
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…