Phenethylamine → HCID 943226, compound

HRID 544370Notes

Reaction equation

HRID 544370 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].ClC(OCC(C)C)=O.[C:31]1([CH2:37][CH2:38][NH2:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[C:8]([O:12][C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH:39][CH2:38][CH2:37][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:19])=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 943226HCID 943226, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (2.8 ml.) was added with stirring to a solution of N-(tert-butyloxycarbonyl)-L-proline (4.3 g.) in tetrahydrofuran (50 ml.) maintained at 0° C. The temperature was lowered to -20° C., isobutyl chloroformate (2.7 ml.) was added, and stirring was continued for15 minutes. 2-Phenylethylamine (2.5 ml.) was then added with continued stirring, and the mixture was allowed to warm to room temperature and filtered. Concentration of the filtrate afforded a solid. Crystallization of the solid from ethyl acetate gave the product in two parts by filtration and in a third part from the filtrate, which was washed with water, aqueous citric acid (5%), saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate, then dried and concentrated. High pressure liquid chromatography of the three parts on silica gel (350 g.) using hexane-ethyl acetate (7:3) as the eluant (200 ml./min.) afforded in fractions 7-8 1-(tert-butyloxycarbonyl)-N-(2-phenylethyl)-L-prolinamide (3.2 g., m.r. 153°-154° C.)

Workup

  1. customwas lowered to -20° C.
  2. waitwas continued for15 minutes
  3. temperatureto warm to room temperature
  4. filtrationfiltered
  5. customConcentration of the filtrate afforded a solid
  6. customCrystallization of the solid from ethyl acetate
  7. customgave the product in two parts
  8. filtrationby filtration
  9. washin a third part from the filtrate, which was washed with water, aqueous citric acid (5%), saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9eb6babda1664dfc8e41ed03f819c624
Source dataset
uspto-grants-1984_05
Patent number
US04450155

Reaction notes

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