(-)-Mandelic acid → (R)-1-(3-Methoxyphenyl)ethylamine

HRID 1781786Notes

Reaction equation

HRID 1781786 reaction equation
C(O)(=O)[C@@H](C1C=CC=CC=1)O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH:17]([NH2:19])[CH3:18]>C(O)(C)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C@H:17]([NH2:19])[CH3:18]

Participants

4

Reactant 2

HCID 11914(-)-Mandelic acidHCID 46120581-(3-Methoxyphenyl)ethanamine

Product 1

HCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 14.0 g (92.0 mmol) of (R)-(-)- mandelic acid (Aldrich, 99+%), 14.0 g (92.7 mmol) of (±) 3-methoxy-α-methylbenzylamine and 500 mL of isopropanol was brought to reflux and gravity filtered while hot. The solution was then seeded at 50° C. with diastereomerically-pure seeds. After cooling to room temperature, the mixture was filtered to afford 10.9 g of a fluffy, white solid. This was recrystallized from 500 mL of isopropanol. The solids were collected then partitioned between ethyl acetate and saturated Na2CO3. The organics were washed with saturated NaCl, dried with Na2SO4, and concentrated to afford 5.8 g (83%) of a yellow oil. NMR analysis of the derived camphorsulfonamide (FIG. 6) indicated that the chemical is enantiomerically pure, to the limits of detection of NMR. This oil was distilled, b.p. 118°-120° C. at aspirator pressure, [α]D =+3.8° (c+1 in 2N HCl). Preliminary results suggest that this compound may form a carbonate upon exposure to air. It is therefore recommended that the chemical be stored under an inert atmosphere.

Workup

  1. temperatureto reflux
  2. filtrationgravity filtered while hot
  3. customwas then seeded at 50° C. with diastereomerically-pure seeds
  4. filtrationthe mixture was filtered
  5. customto afford 10.9 g of a fluffy, white solid
  6. customThis was recrystallized from 500 mL of isopropanol
  7. customThe solids were collected
  8. customthen partitioned between ethyl acetate and saturated Na2CO3
  9. washThe organics were washed with saturated NaCl
  10. dry with materialdried with Na2SO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f20e599b4b974f9f93ef7af1788114bb
Source dataset
uspto-grants-1997_05
Patent number
US05633404

Reaction notes

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