Hydrochloric Acid → HCID 68882717, compound

HRID 1269495Notes

Reaction equation

HRID 1269495 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([CH3:19])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:8]=1)[CH3:5].Cl.[H][H]>CO.[Pt]>[CH3:1][O:2][C:3](=[O:20])[C:4]([CH3:5])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[CH:8]=1)[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 688829912-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 68882717HCID 68882717, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid methyl ester (4.07 g, 15.0 mmol) was dissolved in methanol (40 mL) and followed by the addition of 37% HCl (3.8 mL) and 10% Pt/C (0.41 g). The mixture was shaken with hydrogen under 50 psi at 50° C. in a Parr bottle for 2 h, filtered through a pad of Celite, and rinsed with methanol. After solvent removal, the residue was treated with saturated aqueous Na2CO3 (100 mL) and extracted with ethyl acetate (2×100 mL). The organic extract was washed with water, dried over sodium sulfate, and concentrated to give 3.70 g (89%) of 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid methyl ester as a yellow oil: 1H NMR (CDCl3) δ 1.57 (br m, 1H), 1.60 (s, 6H), 1.78 (br, 1H), 1.86 (br, 1H), 1.97 (brd, 1H), 2.61 (m, 3H), 3.06–3.13 (m, 2H), 3.76 (s, 3H), 6.61 (dd, 1H), 6.70 (s, 1H), 6.83 (d, 1H), 7.14 (t, 1H); MS m/z (relative intensity) 277 (M+, 2), 218 (6), 176 (100).

Workup

  1. filtrationfiltered through a pad of Celite
  2. washrinsed with methanol
  3. customAfter solvent removal
  4. additionthe residue was treated with saturated aqueous Na2CO3 (100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-95a876b899fe4a21a5ed45485f0607c4
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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