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Diisobutylaluminum hydride → ((1r)-1-Phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amine

HRID 2113138
Notes
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Reaction equation

HRID 2113138 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:13]=2)=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:1]1([C@H:7]([NH:9][CH2:10][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:13]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C@H:7]([NH:9][CH2:10][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[CH:13]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 20803221n-((1r)-1-Phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamide

Product 2

HCID 60010447((1r)-1-Phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amineHCID 600105454-(5-{[((1r)-1-Phenylethyl)amino]methyl}-2-methylphenyl)phenol

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a solution of N-((1R)-1-phenylethyl)[3-(4-methoxyphenyl)-4-methylphenyl]carboxamide (0.12 g, 0.34 mmol) in 10 mL of toluene was added DIBAL-H (1 mL, 1.5 mmol). The reaction was then heated to 100 C for 16 hours and cooled to RT. The reaction was quenched with 5 mL of 2N NaOH aq. soln. 100 mL of CH2Cl2 was used to extract the product. The organic phase was washed with 30 mL of brine, dried over Na2SO3 and concentrated in vacuo. The desired products were separated by silica gel column chromatography (30% to 60% EtOAc in hexane) provide ((1R)-1-phenylethyl){[3-(4-methoxyphenyl)-4-methylphenyl]methyl}amine and 4-(5-{[((1R)-1-phenylethyl)amino]methyl}-2-methylphenyl)phenol, which were treated with 1N HCl in Et2O separately to provide the HCl salts as white solids.

Workup

  1. temperatureThe reaction was then heated to 100 C for 16 hours
  2. customThe reaction was quenched with 5 mL of 2N NaOH aq. soln
  3. extractionto extract the product
  4. washThe organic phase was washed with 30 mL of brine
  5. dry with materialdried over Na2SO3
  6. concentrationconcentrated in vacuo
  7. customThe desired products were separated by silica gel column chromatography (30% to 60% EtOAc in hexane)

Sources & evidence

ORD record
ord-5e8f89dde42b4528a0c5cdfe019d2fc5
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07524873B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes