Aluminium lithium hydride → HCID 86668753, compound

HRID 473115Notes

Reaction equation

HRID 473115 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH2:19][C@H:18]([NH:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[CH2:17]3)[CH:12]=1)[C:6](OC)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:29][C:27]([F:28])([F:30])[S:24]([NH:23][C@@H:18]1[CH2:17][C:16]2[C:20](=[CH:21][CH:22]=[C:14]([CH2:13][C:11]3[CH:12]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:4]=[C:5]([CH2:6][OH:7])[CH:10]=3)[CH:15]=2)[CH2:19]1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86668752HCID 86668752, compound

Product 1

HCID 86668753HCID 86668753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-methyl 3-(trifluoromethyl)-5-((2-(trifluoromethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)benzoate (0.135 mmol, 65 mg) in THF (1.5 mL) at 0° C. was added Lithium aluminium hydride (0.405 mmol, 15.37 mg). The whole was stirred at 0° C. for 4 h before the reaction mixture was quenched by the addition of 2N HCl & diluted with DCM. The organics were separated/dried using a hydrophobic frit before being concentrated to dryness and the residue purified by preparative HPLC to give a clear film (29 mg, 47.4%). MS (ESI): m/z [M+NH4]+ 471.5

Workup

  1. customwas quenched by the addition of 2N HCl
  2. additiondiluted with DCM
  3. customThe organics were separated/dried
  4. concentrationbefore being concentrated to dryness
  5. customthe residue purified by preparative HPLC
  6. customto give a clear film (29 mg, 47.4%)

Sources & evidence

ORD record
ord-9b2ea63a6dd4409483f61052ca6ca94d
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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