(-)-Mandelic acid → (1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine

HRID 709418Notes

Reaction equation

HRID 709418 reaction equation
C1C=CC([C@@H](O)C(O)=O)=CC=1.Cl.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]2[CH2:29][C@H:28]2[NH2:30])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C@@H:27]2[CH2:29][C@H:28]2[NH2:30])=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 11914(-)-Mandelic acidHCID 66715085rac-(1R,2S)-2-[4-(benzyloxy)phenyl]cyclopropan-1-amine hydrochloride2×

Product 1

HCID 51888238(1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amineYield 46.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

R-(−)-Mandelic acid (22.2 g, 0.14 mol) was added to a solution of (trans)-2-(4-(benzyloxy)phenyl)cyclopropanamine hydrochloride (intermediate V) (35 g, 0.14 mol) in a mixture of THF and H2O (6:4) (650 mL) and refluxed for 1 h. After formation of a clear solution the reaction mixture was cooled to RT. The solid precipitated formed was filtered, basified with sat. NaHCO3 solution and extracted with ethyl acetate (3×500 mL). The combined organic extracts were washed with water (500 mL), brine (500 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to afford trans 2-(4-(benzyloxy)phenyl)cyclopropanamine (enantiomer-(−)) (14 g, 46.6%) as an off white solid.

Workup

  1. temperaturerefluxed for 1 h
  2. customThe solid precipitated
  3. customformed
  4. filtrationwas filtered
  5. extractionextracted with ethyl acetate (3×500 mL)
  6. washThe combined organic extracts were washed with water (500 mL), brine (500 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7cf3a431b9fc48648938ac6b376dc918
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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