Ammonia → (4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanamide

HRID 537968Notes

Reaction equation

HRID 537968 reaction equation
[NH3:1].CO.[CH3:4][C:5]1[CH:6]=[C:7]([C@@H:12]([OH:20])[CH2:13][CH2:14][C:15](OCC)=[O:16])[CH:8]=[C:9]([CH3:11])[CH:10]=1>>[CH3:4][C:5]1[CH:6]=[C:7]([C@@H:12]([OH:20])[CH2:13][CH2:14][C:15]([NH2:1])=[O:16])[CH:8]=[C:9]([CH3:11])[CH:10]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86626141ethyl (4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanoate

Product 1

HCID 68997524(4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanamide

Procedure

A solution of ammonia in methanol (2.0M; 4.02 mL; 8.03 mmol) was treated with ethyl (4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanoate (Step A; 474 mg; 2.01 mmol) and the resultant solution was stirred at 50° C. for 16 h. The reaction was concentrated in vacuo and the residue purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient) to afford (4S)-4-(3,5-dimethylphenyl)-4-hydroxybutanamide as a white solid. LCMS=190.3 (M+1−18)+. 1H NMR (CDCl3, 500 MHz): δ 7.00 (s, 2H), 6.94 (s, 1H), 5.61 (br s, 1H), 5.40 (br s, 1H), 4.75 (dd, J=7.6, 2.8 Hz, 1H), 2.43-2.39 (m, 2H), 2.34 (s, 6H), 2.12-2.07 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-3e131b177b3e44ffa4d76bbddbf65a65
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

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