Aluminium lithium hydride → HCID 22560290, compound

HRID 983407Notes

Reaction equation

HRID 983407 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][F:15])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:17]([NH:16][CH:13]([CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)[CH2:14][F:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22560188HCID 22560188, compound

Product 1

HCID 22560290HCID 22560290, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyl-3-(1-benzylamino-2-fluoroethyl)pyrrolidin-2-one (7.2 g, 22 mmol, Example 16) in tetrahydrofuran (100 mL) at 0° C. was added lithium aluminum hydride (1M in tetrahydrofuran, 22 mL) dropwise. After 1 hour, the mixture was warmed to room temperature and then quenched after 30 minutes with 0.84 mL water, 0.84 mL 15% sodium hydroxide solution and 2.5 mL water. The reaction mixture was then filtered and concentrated. The crude residue was purified by chromatography (97:3 to 90:10 dichloromethane/methanol) to give the title compound (2.5 g) as a mixture of diastereomers. MSCI: m/z=313 (MH+).

Workup

  1. customquenched after 30 minutes with 0.84 mL water, 0.84 mL 15% sodium hydroxide solution and 2.5 mL water
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated
  4. customThe crude residue was purified by chromatography (97:3 to 90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-9ce1b3d16db144c6ad71790ed5cf99af
Source dataset
uspto-grants-2005_03
Patent number
US06864259B2

Reaction notes

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