Aluminium lithium hydride → HCID 178519578, compound

HRID 2080949Notes

Reaction equation

HRID 2080949 reaction equation
[CH:1]1([N:4]([C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][C:21](OC)=[O:22])[CH2:16][CH2:15]2)[C:5](=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]1([N:4]([C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]2)[C:5](=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178500699HCID 178500699, compound

Product 1

HCID 178519578HCID 178519578, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(trans-4-(N-cyclopropyl-3-fluorobenzamido)cyclohexyl)acetate (0.100 g, 0.30 mmol) in THF (3 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 15 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 50% EtOAc-hexane. The alcohol product was obtained as a sticky white solid (42 mg). MS: 306 (M+1), C18H24FNO2.

Workup

  1. customThe reaction was quenched with saturated NH4Cl (10 mL) after 15 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 50% EtOAc-hexane

Sources & evidence

ORD record
ord-189722c63f02431fb781fb876c389e72
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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