Acetic Acid → {2-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine

HRID 76221Notes

Reaction equation

HRID 76221 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][C:6]([CH2:15][CH:16]=O)([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH2:24].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:18])[CH2:7][C:6]([CH2:15][CH2:16][NH:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([CH3:19])[CH:21]=2)([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 660153-MethylbenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866714262-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde

Product 1

HCID 68314021{2-[2,2-Dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde (61.6 mg, 0.25 mmol), 3-methylbenzylamine (63 μl, 0.5 mmol) and acetic acid (50 μl, 8.6 mmol) in CH2Cl2 (3 ml) was stirred at rt for 1 h before it adding sodium triacetoxyborohydride (106 mg, 0.50 mmol). The resulting mixture was stirred at rt for 18 h. The mix was concentrated and dissolved in MeOH and purified by HPLC to give {2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine as a white solid (35 mg, 40%, m/z: 352.3 [M+H]+ observed).

Workup

  1. stirringThe resulting mixture was stirred at rt for 18 h
  2. concentrationThe mix was concentrated
  3. dissolutiondissolved in MeOH
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-a1af5ac96c35468a8bca66679b51e7de
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Reaction notes

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