3-(2-ETHOXYCARBONYL-ACETYL)-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER → HCID 178451768, compound

HRID 2047118Notes

Reaction equation

HRID 2047118 reaction equation
C(O[C:4](=[O:20])[CH2:5][C:6]([CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1)=O)C.[NH:21]1[CH:25]=[CH:24][C:23]([NH2:26])=[N:22]1>C1(C)C=CC=CC=1>[OH:20][C:4]1[N:22]2[N:21]=[CH:25][CH:24]=[C:23]2[N:26]=[C:6]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9]2)[CH:5]=1

Participants

4

Reactant 2

HCID 247302783-(2-ETHOXYCARBONYL-ACETYL)-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTERHCID 178418806HCID 178418806, compound

Product 1

HCID 178451768HCID 178451768, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of tert-butyl 3-(3-ethoxy-3-oxopropanoyl)pyrrolidine-1-carboxylate (7.00 g, 25 mmol) and 1H-pyrazol-3-amine (2.08 g, 25 mmol) in toluene 30 mL) was heated at 110° C. under argon for 18 h and concentrated in vacuo. The residue was triturated with EtOAc and the solid was collected by filtration and dried in high vacuum to give 6.84 g (90%) of the title compound as a white solid. LC/MS RT=1.40 min (5 min method). Mass calculated for, M+H 305.15, observed 305.15.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with EtOAc
  3. filtrationthe solid was collected by filtration
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-137a73a5b7c2439ebdb5231f3d0959a9
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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