Ethyl trans-crotonate → HCID 11789974, compound

HRID 1656147Notes

Reaction equation

HRID 1656147 reaction equation
C[C@@H:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:3][CH2:4][C:5]1C=C[CH:8]=[CH:7][CH:6]=1.C([Li])CCC.C(OCC)(=[O:26])/C=C/C>C1COCC1>[CH2:2]([N:3]1[C@@H:7]([CH3:8])[CH2:6][C:5](=[O:26])[CH2:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 429065Ethyl trans-crotonateHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 178418339Butyllithium

Product 1

HCID 11789974HCID 11789974, compoundYield 158.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 20.394 g (96.513 mmol) of (S)-alpha-methyl-N-(phenylmethyl)-benzenemethanamine (from Example 5) in 400 mL of THF, cooled to 0° C., was added, over a 10 minute period, 38.61 g (96.525 mmol) of n-butyllithium, and the reaction was stirred for an additional 15 minutes. To this solution was added 10.00 mL (80.427 mmol) of ethyl crotonate with stirring over a 20 minute period, and the solution was stirred for an additional 20 minutes. The reaction was quenched by addition of an excess of saturated ammonium chloride solution, and the mixture was extracted with ether. The ether extract was washed with saturated brine, dried over MgSO4 and concentrated to give a colorless liquid. The crude product was chromatographed on silica gel, eluting with 1:4 ethyl acetate:hexane, and the solvent was removed to afford 24.10 g (92.1%) of the title product as a colorless oil. MS M/Z: 326 (M+H). NMR (CDCl3) δ: 1.13 (d, 3 H, J=7 Hz), 1.16 (t, 3H, J=7 Hz), 1.35 (d, 3H, J=7 Hz), 2.10 (dd, 1H, J=14 Hz, J=6 Hz), 2.36 (dd, 1H, J=14 Hz, J=6 Hz), 3.44 (m, 1H), 3.67 (d, 1H, J=14 Hz), 3.74 (d, 1H, J=14 Hz), 3.88-4.07 (m, 3H), 7.19-7.42 (10H). Anal calc. for C21H27NO2 : C, 77.50; H, 8.36 N, 4.30; found: C, 77.46; H, 8.37; N, 4.28.

Workup

  1. additionwas added, over a 10 minute period
  2. stirringthe solution was stirred for an additional 20 minutes
  3. customThe reaction was quenched by addition of an excess of saturated ammonium chloride solution
  4. extractionthe mixture was extracted with ether
  5. extractionThe ether extract
  6. washwas washed with saturated brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customto give a colorless liquid
  10. customThe crude product was chromatographed on silica gel
  11. washeluting with 1:4 ethyl acetate
  12. customhexane, and the solvent was removed

Sources & evidence

ORD record
ord-12b41f3b92fb4ab69acb538ee786f7cf
Source dataset
uspto-grants-1993_10
Patent number
US05252747

Reaction notes

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