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

HRID 588127Notes

Reaction equation

HRID 588127 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 5 (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 (S)-2-methoxy-2-methyl-1-phenylpropan-1-amine H1NMR (CDCl3, 400 MHz) 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-3d4ac4dce4594a4a872bf543c5a94700
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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