1-Phenethylamine, (+)- → Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate

HRID 736780Notes

Reaction equation

HRID 736780 reaction equation
[CH3:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[C:7](=O)[CH2:6][CH2:5][O:4][CH2:3]1.[CH3:13][C@@H:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[C:7](=[N:21][C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:13])[CH2:6][CH2:5][O:4][CH2:3]1

Participants

5

Reactant 3

HCID 6431891-Phenethylamine, (+)-HCID 2733225Ytterbium triflateHCID 68819284Methyl 3-methyl-4-oxooxane-3-carboxylate

Product 1

HCID 68817214Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 3-methyl-4-oxo-tetrahydro-2H-pyran-3-carboxylate (2.33 g, 13.53 mmol) was dissolved in toluene (150 mL) and treated with R-(+)-α-methylbenzylamine (3.96 mL, 2.3 eq) and ytterbium (III) trifluoromethanesulfonate (252 mg, 0.03 eq). The mixture was heated to reflux under Dean-Stark conditions overnight, and then concentrated to provide crude methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate that was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under Dean-Stark conditions overnight
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2a4d4e368e5946b3877372f7a5253a57
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…