Diisopropylamine → Methyl 1-methyl-2-oxopyrrolidine-3-carboxylate

HRID 2293432

Reaction equation

HRID 2293432 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19].[CH3:20][O:21][C:22](=O)[O:23]C>C1COCC1.CCCCCC.O>[CH3:13][N:14]1[CH2:18][CH2:17][CH:16]([C:22]([O:21][CH3:20])=[O:23])[C:15]1=[O:19]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 12021Dimethyl CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 178418339Butyllithium

Product 1

HCID 12646144Methyl 1-methyl-2-oxopyrrolidine-3-carboxylateYield 25.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of diisopropylamine (11.3 g, 0.11 mol) in THF (150 ml), at -78° was added n-butyl lithium (60 mls of a 1.6M solution in hexane). The solution was stirred for 0.5 hours before adding N-methyl-2-pyrrolidone (10.1 g; 0.1 mol) in THF (50 ml) over a period of 5 minutes. After 0.75 hours. a solution of dimethylcarbonate (10.8 g: 0.12 mols) in THF (30 ml) was added and the reaction mixture allowed to warm to room temperature overnight. The reaction mixture was poured into water (50 ml) and extracted with dichloromethane (3×150 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo. The crude product was chromatographed on silica gel using ethyl acetate/methanol (2:1) as eluant to afford the title product as a clear liquid (4 g). δ(CDCl3) 1.90-2.70 (2H, m, CH2); 2.80 (3H, s, CH3) 3.20-3.60 (3H, m, CH and CH2); 3.70 (3H, s, CO2CH3).

Workup

  1. waitAfter 0.75 hours
  2. extractionextracted with dichloromethane (3×150 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-2eba0e26e0714ad1bd2524706e712c96
Source dataset
uspto-grants-1997_11
Patent number
US05686463

Linked notes

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