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

HRID 265813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265813
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-82c2bcea1f2c4c5fae50ffdb2dbfd179
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648540

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