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

HRID 337007Notes

Reaction equation

HRID 337007 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-c5f61f9d15304c0b8f1ab0f526173edd
Source dataset
uspto-grants-2014_11
Patent number
US08889710B2

Reaction notes

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