HCID 86681319, compound → HCID 89498330, compound

HRID 1778933Notes

Reaction equation

HRID 1778933 reaction equation
[CH:1]1([CH:7]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH2:8][CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1>[CH:1]1([CH:7]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86681319HCID 86681319, compound

Product 1

HCID 89498330HCID 89498330, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of EXAMPLE 152A (2.42 g) in toluene (20 mL) diisobutylaluminum hydride (28.2 mL) was added at −78° C. The reaction mixture was stirred for 60 minutes. The reaction mixture was quenched with methanol (10 mL), 1M aqueous HCl (200 mL) and washed with saturated NaHCO3. The organic layer was dried over magnesium sulfate, filtered and concentrated. The product was purified by flash chromotography (silica gel, 10-100% ethyl acetate/hexanes) to provide the title compound.

Workup

  1. customThe reaction mixture was quenched with methanol (10 mL), 1M aqueous HCl (200 mL)
  2. washwashed with saturated NaHCO3
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromotography (silica gel, 10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0f570be8a2dd4a35a495a5b092456a69
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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