HCID 45739920, compound → HCID 58654344, compound

HRID 1170525Notes

Reaction equation

HRID 1170525 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:25])[NH:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:20]1[C:19]2[CH:23]=[CH:24][C:16]([CH2:15][NH:14][C:13]([CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[O:25])=[CH:17][C:18]=2[O:22][CH2:21]1

Participants

3

Reactant 1

HCID 45739920HCID 45739920, compound

Product 1

HCID 58654344HCID 58654344, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

2-[(Benzo[1,3]dioxol-5-ylmethyl)-carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (278 mg, 0.80 mmol) was dissolved in DCM:TFA (1:1, 6 mL) and stirred at room temperature for 3 hours. After this period, the solution was concentrated down under vacuum. The crude material was diluted in DCM (50 mL) and washed with 1M NaOH (aq) (50 mL) to afford the crude residue. The crude product was purified by Flash chromatography (0-10% methanol/DCM gradient) to afford 85.1 mg (43%) of pyrrolidine-2-carboxylic acid (benzo[1,3]dioxol-5-ylmethyl)-amide. [M+H]+ 249.08.

Workup

  1. waitAfter this period
  2. concentrationthe solution was concentrated down under vacuum
  3. additionThe crude material was diluted in DCM (50 mL)
  4. washwashed with 1M NaOH (aq) (50 mL)
  5. customto afford the crude residue
  6. customThe crude product was purified by Flash chromatography (0-10% methanol/DCM gradient)

Sources & evidence

ORD record
ord-f4ce68ebd12345a2851a37ea4566464b
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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