Triethylamine → 1-Oxo-1-(2-(pyrrolidin-1-yl)cyclopent-1-enyl)propan-2-yl acetate

HRID 240896Notes

Reaction equation

HRID 240896 reaction equation
[C:1]([O:4][CH:5]([CH3:9])[C:6](Cl)=[O:7])(=[O:3])[CH3:2].[C:10]1([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH:11]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:4][CH:5]([CH3:9])[C:6](=[O:7])[C:11]1[CH2:12][CH2:13][CH2:14][C:10]=1[N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-HCID 45474922-Acetoxypropionyl Chloride

Product 1

HCID 710141241-Oxo-1-(2-(pyrrolidin-1-yl)cyclopent-1-enyl)propan-2-yl acetateYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Add dropwise a solution of 1-chloro-1-oxopropan-2-yl acetate (600 g, 3.98 mol) in toluene (1200 mL) to a solution of 1-cyclopent-1-enyl-pyrrolidine (546.7 g, 3.98 mol) and triethyl amine (483.9 g, 4.78 mol) in toluene (2400 mL). Reflux the mixture for overnight. Filter the mixture and concentrate the filtration to give crude 1-oxo-1-(2-(pyrrolidin-1-yl)cyclopent-1-enyl)propan-2-yl acetate (952 g), which is used in next step without further purification. 1H NMR (CDCl3, 400 MHz): δ 5.27 (m, 1H), 3.56 (m, 2H), 3.16 (m, 2H), 2.83 (m, 1H), 2.58 (m, 3H), 2.10 (s, 3H), 1.93 (m, 2H), 1.82 (m, 4H), 1.36 (d, J=7.2, 3H).

Workup

  1. temperatureReflux the mixture for overnight
  2. filtrationFilter the mixture
  3. concentrationconcentrate
  4. filtrationthe filtration

Sources & evidence

ORD record
ord-e6f5be68a13a4cfc84f44c25f1ade69f
Source dataset
uspto-grants-2014_02
Patent number
US08648081B2

Reaction notes

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