(alphaR,betaR)-beta-ethyl-N,N,alpha-trimethyl-3-(phenylmethoxy)benzenepropanamide → (alphaR,betaR)-beta-ethyl-3-hydroxy-N,N,alpha-trimethylbenzenepropanamide

HRID 1771014Notes

Reaction equation

HRID 1771014 reaction equation
[CH2:1]([C@@H:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17]CC2C=CC=CC=2)[CH:12]=1)[C@@H:4]([CH3:10])[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])[CH3:2]>CO.[Pd]>[CH2:1]([C@@H:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1)[C@@H:4]([CH3:10])[C:5]([N:7]([CH3:8])[CH3:9])=[O:6])[CH3:2]

Participants

4

Reactant 1

HCID 60164737(alphaR,betaR)-beta-ethyl-N,N,alpha-trimethyl-3-(phenylmethoxy)benzenepropanamide

Product 1

HCID 58555147(alphaR,betaR)-beta-ethyl-3-hydroxy-N,N,alpha-trimethylbenzenepropanamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 5 (3.0 g, 9 mmol) was dissolved in methanol, 5% Pd—C (300 mg) was added therein, after it was purged with hydrogen for three times, the reaction was carried out with stirring at room temperature for 1 hr. Then the reaction solution was filtered to remove Pd—C, the residue was washed with methanol for 3 times, and the organic phases are combined and concentrated to give the target 2.0 g, yield: 95%. 1HNMR (300 MHz, CDCl3): δ 7.2 (1H, m), 6.7-6.8 (3H, m), 2.8-2.9 (1H, m), 2.7-2.8 (1H, m), 2.6 (3H, s), 2.5 (3H, s), 1.8-1.9 (1H, m), 1.4-1.6 (1H, m), 1.1 (3H, d, J=6.2), 0.8 (3H, t, J=6.8, 14.1). ESI-MS: 236.4 (M+H).

Workup

  1. customafter it was purged with hydrogen for three times
  2. filtrationThen the reaction solution was filtered
  3. customto remove Pd—C
  4. washthe residue was washed with methanol for 3 times
  5. concentrationconcentrated
  6. customto give the target 2.0 g, yield: 95%

Sources & evidence

ORD record
ord-94255fe32674423aa809441c0cd1cace
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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