Aluminium lithium hydride → HCID 53779306, compound

HRID 428321Notes

Reaction equation

HRID 428321 reaction equation
[CH:1]([N:4]([CH:31]([CH3:33])[CH3:32])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([C:20](=[O:22])[CH3:21])[CH:17]=[CH:16][C:15]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:31]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([CH:20]([OH:22])[CH3:21])[CH:17]=[CH:16][C:15]=1[O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 54165959(R)-N,N-Diisopropyl-3-(5-acetyl-2-benzyloxyphenyl)-3-phenylpropanamine

Product 1

HCID 53779306HCID 53779306, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Diisopropyl-3(R)-(5-acetyl-2-benzyloxyphenyl)-3-phenylpropanamine, prepared as described in Example 13.1, (3.5 g, 7.90 mmol) dissolved in dry THF was added to LiAlH4 (0.2 g, 5.41 mmol). After 2 hours of stirring, additional LiAlH4 (50 mg, 1.32 mmol) was added and the reaction mixture was stirred for 1.5 hours. The reaction was quenched and the solvent evaporated. The residue was chromatographed on silica (toluene-E3N 90:10) to give 2.74 g (78%) of an oil that crystallised slowly upon storage at room temperature.

Workup

  1. stirringthe reaction mixture was stirred for 1.5 hours
  2. customThe reaction was quenched
  3. customthe solvent evaporated
  4. customThe residue was chromatographed on silica (toluene-E3N 90:10)

Sources & evidence

ORD record
ord-781c9a62d6644d3a841abfb0b2c04f97
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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