Triethylamine → (S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992288Notes

Reaction equation

HRID 992288 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1.C(N(CC)CC)C.[C:21]12([C:31](Cl)=[O:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>CN(C=O)C>[CH2:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:31]([C:21]23[CH2:30][CH:25]4[CH2:24][CH:23]([CH2:29][CH:27]([CH2:26]4)[CH2:28]2)[CH2:22]3)=[O:32])[CH2:3]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidine

Product 1

HCID 9884297(S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-Amino-1-benzylpyrrolidine (10 g) and triethylamine (24 ml) were dissolved in DMF (100 ml). Under ice-cooling, 1-adamantanecarbonyl chloride (12.4 g) was added thereto, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure. To the obtained residue was added ethyl acetate and the mixture was washed with saturated brine. 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 and IPE was added to the obtained residue. The precipitated crystals were collected by filtration to give (S)-N-(1-benzylpyrrolidin-3-yl)-1-adamantanecarboxamide (14.8 g), melting point 130-132° C.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure
  3. additionTo the obtained residue was added ethyl acetate
  4. washthe mixture was washed with saturated brine
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe obtained eluate was concentrated
  7. additionIPE was added to the obtained residue
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-f50cc3d55cf34034827cb4f2a2a80aee
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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