Aluminium lithium hydride → HCID 178519526, compound

HRID 2080948Notes

Reaction equation

HRID 2080948 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]=[CH:8][C:7]=2[F:12])[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]=[CH:8][C:7]=2[F:12])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178500696HCID 178500696, compound

Product 1

HCID 178519526HCID 178519526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(trans-4-(N-cyclopropyl-2-fluorobenzamido)cyclohexyl)acetate (0.100 g, 0.30 mmol) in THF (3 mL) was added lithium aluminum hydride (1.0 M solution in THF) (0.33 ml, 0.33 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, 50% EtOAc-hexane. The alcohol product was obtained as a sticky white solid (74 mg). MS: 306 (M+1), C18H24FNO2.

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, 50% EtOAc-hexane

Sources & evidence

ORD record
ord-a5112bd41eab42ceb261c03441df427a
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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