Diphenylacetic Acid → (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)diphenylacetamide

HRID 992295Notes

Reaction equation

HRID 992295 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][C@H:18]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19]1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C=O)C>[C:25]1([CH2:24][CH2:23][N:20]2[CH2:21][CH2:22][C@H:18]([NH:17][C:8](=[O:10])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:19]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 10774056(3S)-1-(2-Phenylethyl)-3-pyrrolidinamine

Product 1

HCID 59915928(S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)diphenylacetamideYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diphenylacetic acid (0.75 g) and (S)-3-amino-1-(2-phenylethyl)pyrrolidine (0.67 g) were dissolved in DMF (10 ml), and triethylamine (1.4 ml) was added thereto, which was followed by addition of diethyl cyanophosphate (0.67 ml) under ice-cooling. After completion of the reaction, the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate, washed successively with an aqueous potassium carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (chloroform:methanol=30:1). The obtained eluate was concentrated to give (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)diphenylacetamide (0.77 g). The obtained compound was dissolved in acetone (3 ml), and a solution of oxalic acid (0.18 g) in acetone (3 ml) was added thereto. The precipitated crystals were collected by filtration and washed with acetone to give (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)diphenylacetamide oxalate, melting point 191-192° C.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in ethyl acetate
  5. washwashed successively with an aqueous potassium carbonate solution and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. concentrationThe obtained eluate was concentrated

Sources & evidence

ORD record
ord-90fa2acfdd9242de8db1528983a5b218
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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