Hydrochloric Acid → 2-(N-(5-bromo-2-(phenethyl)benzyl)amino)-2-methylpropan-1-ol

HRID 355758Notes

Reaction equation

HRID 355758 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)[CH:7]=1.CC(C[AlH]CC(C)C)C.Cl>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:6]([CH:7]=1)[CH2:8][NH:12][C:11]([CH3:14])([CH3:13])[CH2:10][OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 226755072-(5-Bromo-2-(phenethyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

Product 1

HCID 226755732-(N-(5-bromo-2-(phenethyl)benzyl)amino)-2-methylpropan-1-olYield 70.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 2-(5-bromo-2-(phenethyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole (20 g) in diethyl ether (70 ml) at 0° C. was added DIBAL (168 ml, 1 Mol solution in CH2Cl2). The mixture was stirred at ambient temperature for 18 hours and cooled to 0° C. Aqueous 2N HCl was added to destroy excess DIBAL, the resulting solid was filtered off and suspended in a mixture of water and ethyl acetate. Triethylamine was added until the white solid was dissolved. The organic layer was separated, dried (MgSO4) and evaporated to give 2-(N-(5-bromo-2-(phenethyl)benzyl)amino)-2-methylpropan-1-ol (14.21 g).

Workup

  1. temperaturecooled to 0° C
  2. customto destroy excess DIBAL
  3. filtrationthe resulting solid was filtered off
  4. additionsuspended in a mixture of water and ethyl acetate
  5. additionTriethylamine was added until the white solid
  6. dissolutionwas dissolved
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-65a5a38003884426ac5daf66832d92c6
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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