HCID 17756287, compound → HCID 69018223, compound

HRID 491585Notes

Reaction equation

HRID 491585 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:16]=1[C:24]([F:27])([F:26])[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.O1CCOCC1>[NH2:21][C:19]1[CH:18]=[CH:17][C:16]([C:24]([F:27])([F:25])[F:26])=[C:15]([CH:20]=1)[O:14][CH2:13][C@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

4

Reactant 1

HCID 17756287HCID 17756287, compound

Product 1

HCID 69018223HCID 69018223, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-2-(5-Nitro-2-trifluoromethyl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.19 g, 5.60 mmol) was dissolved in 40 mL MeOH and 10 mL dioxane. To the nitrogen-degassed solution was added 10% Pd/C (0.3 g). The reaction was stirred vigorously at RT under 1 atm H2 gas for 42 h. The reaction was filtered through Celite® and concentrated in vacuo to yield the title compound as a white foam. MS (MNa+)=383.3; Calc'd 360.38 for C17H23F3N2O3.

Workup

  1. customTo the nitrogen-degassed solution
  2. additionwas added 10% Pd/C (0.3 g)
  3. filtrationThe reaction was filtered through Celite®
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d07cdfcd394a4546851c93a6335194db
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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