Triethylamine → cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

HRID 1906283Notes

Reaction equation

HRID 1906283 reaction equation
ClC(OCC)=O.[OH:7][CH:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=O)[C:9]1=[O:17].C(N(CC)CC)C.[CH3:25][C@H:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([CH3:32])[N:27]1[CH2:33][CH2:34][NH2:35]>C(Cl)(Cl)Cl>[CH3:25][C@H:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([CH3:32])[N:27]1[CH2:33][CH2:34][NH:35][C:14](=[O:16])[CH2:13][N:10]1[CH2:11][CH2:12][CH:8]([OH:7])[C:9]1=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 7837022-(cis-2,6-Dimethyl-1-piperidinyl)ethanamineHCID 19817647(R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetic acid

Product 1

HCID 3069833cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

1.2 ml of ethyl chloroformate are placed in 12 ml of chloroform, whereupon there are added dropwise at -30° within 30 minutes 2.0 g of (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetic acid and 1.74 ml of triethylamine dissolved in 50 ml of chloroform. After stirring at a temperature between -2° and -10° for 12 minutes, 2.07 g of 94.7% cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine dissolved in 10 ml of chloroform are added dropwise. The mixture is left to stand at room temperature overnight. Thereupon, the mixture is evaporated and the residue (6 g) is chromatographed on 120 g of aluminum oxide (activity grade III, neutral). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with acetonitrile and ethanol has a melting point of 128°-130° after repeated chromatography on aluminum oxide and recrystallization from ethyl acetate.

Workup

  1. additionare added dropwise
  2. waitThe mixture is left
  3. waitto stand at room temperature overnight
  4. customThereupon, the mixture is evaporated
  5. customthe residue (6 g) is chromatographed on 120 g of aluminum oxide (activity grade III, neutral)
  6. washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with acetonitrile and ethanol
  7. customon aluminum oxide and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3bddd6bf3e094a63afb25a10344b35e4
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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