3,3-Difluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine → HCID 58980809, compound

HRID 1181357Notes

Reaction equation

HRID 1181357 reaction equation
[F:1][C:2]1([F:21])[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[O:19][CH3:20])[CH2:3]1>CCOC(C)=O.[Pd]>[F:21][C:2]1([F:1])[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=2[O:19][CH3:20])[CH2:3]1

Participants

4

Reactant 1

HCID 589808943,3-Difluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine

Product 1

HCID 58980809HCID 58980809, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3,3-Difluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine (0.173 g, 0.5728 mmol) was dissolved in EtOAc (5 mL). 10% Pd/C (0.017 g) was added. The reaction was stirred under 1 atm of H2. for 18 h. The mix was then filtered through celite and the celite washed with EtOAc (3×10 mL). The organics were concentrated to give 0.1389 g (0.5107 mmol, 89%) of the product as a red oil. 1H NMR (CDCl3) δ 6.73 (d, 1H, J=8.4 Hz), 6.29 (s, 1H), 6.19 (d, 1H, J=8.4 Hz), 4.02 (t, 2H, J=5.8 Hz), 3.80 (s, 3H0, 3.04 (t, 2H, J=13.4 Hz), 2.87 (m, 4H), 2.27 (m, 2H).

Workup

  1. filtrationThe mix was then filtered through celite
  2. washthe celite washed with EtOAc (3×10 mL)
  3. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-592bbccb05bb485ca2e779e865f8d215
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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