Water → HCID 178520509, compound

HRID 342126Notes

Reaction equation

HRID 342126 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8](OCC)=[O:9])[N:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][OH:9])[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178471154HCID 178471154, compound

Product 1

HCID 178520509HCID 178520509, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester from Step A (120 g, 71.4 mmol) in dry THF (230 mL) at 0° C. was added LAH (2.99 g, 78.6 mmol) portionwise over 30 min. The mixture was stirred for 2 h at room temperature then cooled back to 0° C. and H2O (4.2 mL) was added (care|) dropwise. This was followed by the dropwise addition of 10.6 mL of 1N NaOH then the resulting slurry was stirred at room temperature for 1 h. After filtration through celite washing with EtOAc, the solvent was removed to give the title compound as a clear oil (8.16 g). 1H NMR (CD3OD): δ 1.84 (2H, pentet), 2.68 (2H, t), 3.58 (2H, t), 6.88 (1H, s), 7.80 (1H, s).

Workup

  1. temperaturethen cooled back to 0° C.
  2. stirringthe resulting slurry was stirred at room temperature for 1 h
  3. filtrationAfter filtration
  4. washthrough celite washing with EtOAc
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-0964826ae62c4609bf17029ace9192c6
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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