Water → HCID 24830315, compound

HRID 1025357Notes

Reaction equation

HRID 1025357 reaction equation
C([O:3][C:4]([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:28])[C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])=[CH:14][CH:13]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[OH:3][CH2:4][C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:28])[C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59517952HCID 59517952, compound

Product 1

HCID 24830315HCID 24830315, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of Compound 99 (645 mg, 1.67 mmol) in THF (10 mL) was added LAH (320 mg, 8.4 mmol) at room temperature. After 10 min, the reaction was added 1N NaOH (5 mL) and H2O (10 mL) and extracted with ethyl acetate (EtOAc) (30 mL). The organic phase was collected, dried and concentrated. Column chromatography afforded Compound 22 (485 mg, 85%). 1H NMR (300 MHz, CDCl3) δ 7.80 (s, 1H), 7.59-7.56 (m, 2H), 7.45-7.35 (m, 1H), 7.17-7.13 (m, 2H), 7.13-6.94 (m, 2H), 3.95 (s, 2H), 2.31-2.21 (m, 4H), 1.78-1.64 (m, 4H); ESMS cacld (C20H13F2NO2): 343.1; found: 344.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate (EtOAc) (30 mL)
  2. customThe organic phase was collected
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8373b2e90cb142d9927c1068e0a0d6f0
Source dataset
uspto-grants-2014_05
Patent number
US08729069B2

Reaction notes

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