Aluminium lithium hydride → HCID 86687111, compound

HRID 630825Notes

Reaction equation

HRID 630825 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:11][C:12](=O)[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]1[N:24]2[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]2=[N:22][N:21]=1)(C)(C)C>C1COCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]2[N:24]([C:20]([C@@H:16]3[CH2:17][CH2:18][CH2:19][N:15]3[CH2:14][CH2:13][CH2:12][OH:11])=[N:21][N:22]=2)[CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 89623868HCID 89623868, compound

Product 1

HCID 86687111HCID 86687111, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride solution (2M in THF, 1.64 mL, 3.28 mmol) was added to a solution of Intermediate 84d (550 mg, 1.64 mmol) in THF (15.0 mL) at −10° C. The reaction was stirred for 1 h then quenched by dropwise addition of water (125 μL), sodium hydroxide (3M aqueous, 125 μL) and water (375 μL). The reaction was stirred for 10 min then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 2-10% (2M NH3 in MeOH) in DCM, to give the title compound (145 mg, 33%). LCMS (Method 4): Rt 0.32 mins, m/z 265.2 [MH+].

Workup

  1. customthen quenched by dropwise addition of water (125 μL), sodium hydroxide (3M aqueous, 125 μL) and water (375 μL)
  2. stirringThe reaction was stirred for 10 min
  3. customthen partitioned between EtOAc and water
  4. extractionThe aqueous layer was then extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-1ea2fe3dc0bc4ea4a334cace1fd8d085
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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