1,1-Dimethylethyl 3-(2-methyl-3-nitrophenoxy)-1-pyrrolidinecarboxylate → HCID 22643441, compound

HRID 2414775Notes

Reaction equation

HRID 2414775 reaction equation
[CH3:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1>C(O)C.[Pd]>[NH2:21][C:20]1[C:2]([CH3:1])=[C:3]([CH:17]=[CH:18][CH:19]=1)[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:6]1

Participants

4

Reactant 1

HCID 226434401,1-Dimethylethyl 3-(2-methyl-3-nitrophenoxy)-1-pyrrolidinecarboxylate

Product 1

HCID 22643441HCID 22643441, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of t-butyl 3-(2-methyl-3-nitrophenoxy)pyrrolidin-1-Carboxylate (11.0 g, 34.2 mmol) and 10% Pd/C (0.55 g) in ethanol is hydrogenated (45 psi) at room temperature overnight. After filtering off the catalyst, the filtrate is concentrated to afford the title compound as an off-white solid, 9.98 g, mp 137° C., identified by NMR and mass spectral analyses.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationAfter filtering off the catalyst
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-e446badad73f494ab9b4ae330b406fec
Source dataset
uspto-grants-2004_11
Patent number
US06815456B2

Reaction notes

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