Water → HCID 24830315, compound

HRID 1160742Notes

Reaction equation

HRID 1160742 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, 1 H), 7.59-7.56 (m, 2 H), 7.45-7.35 (m, 1 H), 7.17-7.13 (m, 2 H), 7.13-6.94 (m, 2 H), 3.95 (s, 2 H), 2.31-2.21 (m, 4 H), 1.78-1.64 (m, 4 H); ESMS cacld (C20H19F2NO2): 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-d3d75468893e494c96f765d035ca1f05
Source dataset
uspto-grants-2010_10
Patent number
US07816535B2

Reaction notes

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