Water → HCID 67409606, compound

HRID 714630Notes

Reaction equation

HRID 714630 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](OC)=[O:14])[N:10]=[CH: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])[N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 67409554HCID 67409554, compound

Product 1

HCID 67409606HCID 67409606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 mg (0.21 mmol) of the compound from Example 34A were dissolved in 1 ml of THF, and 222 μl (0.22 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 34 mg (56% of theory) of the target compound in a purity of 73%.

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-3b4655fd1a8e48aa8489a875b4bd2df8
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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