Diisopropylethylamine → Methyl 1-[2-[2-(2-oxo-1-piperidinyl)phenyl]ethyl]-3-pyrrolidineacetate

HRID 2178536Notes

Reaction equation

HRID 2178536 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]2=[O:26])(=O)=O)=CC=1.C(N(C(C)C)CC)(C)C.[CH3:36][O:37][C:38](=[O:45])[CH2:39][CH:40]1[CH2:44][CH2:43][NH:42][CH2:41]1>CN(C=O)C>[O:26]=[C:21]1[CH2:22][CH2:23][CH2:24][CH2:25][N:20]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][CH2:12][N:42]1[CH2:43][CH2:44][CH:40]([CH2:39][C:38]([O:37][CH3:36])=[O:45])[CH2:41]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13424175Methyl 2-(pyrrolidin-3-yl)acetateHCID 89500606HCID 89500606, compound

Product 1

HCID 89506053Methyl 1-[2-[2-(2-oxo-1-piperidinyl)phenyl]ethyl]-3-pyrrolidineacetateYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl 4-methylbenzenesulfonate a2-3 (2.85 g, 7.65 mmol, 1 eq) in DMF (10 ml) at room temperature are added diisopropylethylamine (2.65 ml, 15.30 mmol, 2 eq) and methylpyrrolidin-3-ylacetate a13-0 (1.08 g, 7.65 mmol, 1 eq). The mixture is stirred at 80° C. overnight. The solvent is removed under vacuum. The residue obtained is purified by chromatography over silicagel (eluent: CH2Cl2/EtOH 95/5) to afford 1.05 g of methyl (1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)acetate a13-1 as a yellow oil.

Workup

  1. customThe solvent is removed under vacuum
  2. customThe residue obtained
  3. customis purified by chromatography over silicagel (eluent: CH2Cl2/EtOH 95/5)

Sources & evidence

ORD record
ord-c0ef4849fa834cdb89ae84b3588218ae
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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