Aluminium lithium hydride → HCID 178519395, compound

HRID 2080952Notes

Reaction equation

HRID 2080952 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][C:19](OC)=[O:20])[CH2:14][CH2:13]2)[CH:9]2[CH2:11][CH2:10]2)=[O:7])=[C:4]([F:25])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([CH:9]2[CH2:11][CH2:10]2)[C@H:12]2[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][OH:20])[CH2:16][CH2:17]2)=[O:7])=[C:4]([F:25])[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178500695HCID 178500695, compound

Product 1

HCID 178519395HCID 178519395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(trans-4-(4-bromo-N-cyclopropyl-2-fluorobenzamido)cyclohexyl)acetate (0.050 g, 0.12 mmol) in THF (2 mL) was added lithium aluminum hydride (1.0 M solution in THF) (0.15 ml, 0.15 mmol) at 0° C. The reaction was quenched with saturated NH4Cl (10 mL) after 30 minutes. The mixture was extracted with EtOAc twice. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by prep TLC eluting with 5% MeOH—CH2Cl2 and 50% EtOAc-hexane. The desired alcohol product was obtained as a white solid (15 mg). MS: 386 (M+1), C18H23BrFNO2.

Workup

  1. customThe reaction was quenched with saturated NH4Cl (10 mL) after 30 minutes
  2. extractionThe mixture was extracted with EtOAc twice
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by prep TLC
  6. washeluting with 5% MeOH—CH2Cl2 and 50% EtOAc-hexane

Sources & evidence

ORD record
ord-854c0b0a0e7947288adf2851cd8fd641
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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