Methyl Benzoate → Pyrrolidin-3-yl Benzoate

HRID 1972112Notes

Reaction equation

HRID 1972112 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:15]C[CH:13](O)[CH2:12]1.C(OC(C)C)(C)C.O1CCOCC1>>[C:1]([O:9][CH:10]1[CH2:13][CH2:12][NH:11][CH2:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7150Methyl BenzoateHCID 982104-HydroxypyrrolidineHCID 67198123Dioxane diisopropyl ether

Product 1

HCID 9799108Pyrrolidin-3-yl BenzoateYield 66%

Procedure

In an argon atmosphere, a mixture of methyl benzoate (3.0 mmol), pyrrolidin-3-ol (3.6 mmol), Zn4(OCOCF3)6O (1.25 mol % in terms of mole number) and diisopropyl ether/1,4-dioxane (3/1) (5.0 ml) was heated to reflux for 46 hours, and as a result, pyrrolidin-3-yl benzoate was obtained at a yield of 66%. The yield of N-benzoylpyrrolidin-3-yl benzoate was 34%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 46 hours

Sources & evidence

ORD record
ord-efd9be70c15b4c4b88fa232304395378
Source dataset
uspto-grants-2013_04
Patent number
US08431709B2

Reaction notes

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