HCID 118271795, compound → (αS)-α-(1-Methoxy-1-methylethyl)benzenemethanamine

HRID 590792Notes

Reaction equation

HRID 590792 reaction equation
[CH3:1][O:2][C:3]([CH3:31])([CH3:30])[C@H:4]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:5](CC1C=CC(OC)=CC=1)CC1C=CC(OC)=CC=1>CO.[Pd]>[CH3:1][O:2][C:3]([CH3:31])([CH3:30])[C@H:4]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH2:5]

Participants

4

Reactant 1

HCID 118271795HCID 118271795, compound

Product 1

HCID 57791001(αS)-α-(1-Methoxy-1-methylethyl)benzenemethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-2-methoxy-N,N-bis(4-methoxybenzyl)-2-methyl-1-phenylpropan-1-amine (0.7 g, 1.67 mmol) in anhydrous MeOH was added Pd on C (0.1 g) and the contents were stirred at ambient temperature in H2 atmosphere. After 14 h, the reaction mixture was filtered through a pad of celite and the volatiles were removed under reduced pressure. The residue thus obtained was further purified by preparative HPLC to afford the title compound. H1NMR (ppm, 400 MHz, CDCl3) δ 7.45-7.44 (m, 2H), 7.35-7.33 (m, 3H), 4.1 (s, 1H), 3.32 (s, 3H), 1.2 (s, 3H), 1.12 (s, 3H).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue thus obtained
  4. customwas further purified by preparative HPLC

Sources & evidence

ORD record
ord-010482e02de149218431703cedb3e785
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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