Water → HCID 15086859, compound

HRID 1885545Notes

Reaction equation

HRID 1885545 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[NH2:11][C:12]1[C:17]([CH2:18][O:19][CH3:20])=[C:16]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:15]([C:28](OC)=[O:29])=[C:14]([CH:32]([CH3:34])[CH3:33])[N:13]=1.C1(C)C=CC=CC=1.O>C(OCC)(=O)C>[NH2:11][C:12]1[C:17]([CH2:18][O:19][CH3:20])=[C:16]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:15]([CH2:28][OH:29])=[C:14]([CH:32]([CH3:34])[CH3:33])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 15086858HCID 15086858, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15086859HCID 15086859, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

140 ml (210 mmol) of a 1.5 M solution of diisobutylaluminum hydride are added dropwise at 78° C. to -75° C. under argon to a solution of 23.1 g (70 mmol) of the compound of Example 30 in 1 1 of toluene and the mixture is stirred at this temperature for 1 h. While it is allowed to warm, 40 ml of water and 50 ml of ethyl acetate are added dropwise, kieselguhr is added, filtered off with suction and washed with ethyl acetate. The aqueous phase is extracted with ethyl acetate, and the combined organic phases are washed with saturated NaCl solution and dried over sodium sulphate. The solution is concentrated to dryness and the residue is thoroughly stirred in ether.

Workup

  1. temperatureto warm
  2. additionkieselguhr is added
  3. filtrationfiltered off with suction
  4. washwashed with ethyl acetate
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. washthe combined organic phases are washed with saturated NaCl solution
  7. dry with materialdried over sodium sulphate
  8. concentrationThe solution is concentrated to dryness
  9. stirringthe residue is thoroughly stirred in ether

Sources & evidence

ORD record
ord-0e702922357e403d95e92c71b724afb2
Source dataset
uspto-grants-1992_09
Patent number
US05145857

Reaction notes

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