Reaktion #1123575

Reaktionsgleichung

(R)-4-(6-(cis-4-phenyl-cyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

lithium hydroxide

ethanol

water

→

product

Ausbeute 41.3%

(R)-2-amino-2-(6-(cis-4-phenylcyclohexyloxy)naphthalen-2-yl)propan-1-ol

Ausbeute 41.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux overnight
3. 3
   Sonstigereaction complete
4. 4
   SonstigeThe solvent was removed under vacuum
5. 5
   Sonstigethe residue was partitioned between water and CH2Cl2
6. 6
   ExtraktionThe aqueous layer was extensively is extracted with CH2Cl2
7. 7
   TrocknenThe combined organic phase was dried over Na2SO4
8. 8
   Sonstigesubjected to chromatographic purification with CH2Cl2/MeOH (10:90 to 80:20)
9. 9
   Sonstigeto give the product
10. 10
    SonstigeA final purification on Gilson HPLC 0.1% TFA-ACN/H2O

Vorschrift

The mixture of (R)-4-(6-(cis-4-phenyl-cyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (160 mg, 0.00040 mol) and lithium hydroxide (100 mg, 0.0044 mol) in ethanol (4 mL, 0.08 mol) and water (0.9 mL, 0.05 mol) was heated to reflux overnight. LCMS showed reaction complete. The solvent was removed under vacuum and the residue was partitioned between water and CH2Cl2. The aqueous layer was extensively is extracted with CH2Cl2. The combined organic phase was dried over Na2SO4. The concentrated residue was taken up into DCM and subjected to chromatographic purification with CH2Cl2/MeOH (10:90 to 80:20) to give the product. A final purification on Gilson HPLC 0.1% TFA-ACN/H2O to gave the product as a white solid (62.0 mg, 41% yield). LCMS 359.33 ([M−NH2]+, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 1.71 (brd, J=13.1 Hz, 2H), 1.78 (s, 3H), 1.83 (brd, J=14.7 Hz, 2H), 1.98 (dd, J=13.7, 11.1 Hz, 2H), 2.24 (d, J=12.6 Hz, 2H), 2.67 (dd, J=11.6, 11.5 Hz, 1H), 3.82 (d, J=11.7 Hz, 1H), 3.92 (d, J=11.7 Hz, 1H), 4.84 (brs, 1H), 7.16 (m, 1H), 7.27-7.32 (m, 6H), 7.52 (d, J=8.7 Hz, 1H), 7.85 (m, 3H).

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