Pyrrolidine → HCID 16738249, compound

HRID 23992Notes

Reaction equation

HRID 23992 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([N+]([O-])=O)=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1CCC[CH2:23]1>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][CH:17]=1)[NH:22][CH:23]=[CH:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 69734823HCID 69734823, compound

Product 1

HCID 16738249HCID 16738249, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
120 °C

Procedure

5 (2-Benzyloxy-ethoxy)-2-nitro-toluene (12.4 g, 43.0 mmol), N-N-dimethylformamide dimethyl acetal (6.55 g, 51.6 mmol) and pyrrolidine (3.68 g, 51.6 mmol) were dissolved in N-N-dimethylformamide (25 mL). The mixture was heated to 120° C. for 16 h. The solvent was evaporated under vacuum and the crude reaction was dissolved in 70% ethyl acetate/methanol (250 mL). The reaction was placed in a Parr Hydrogenator under a hydrogen atmosphere for 16 h with 10% palladium on carbon [10% w/w] (3.00 g) at 50 psi. The reaction was filtrated over celite and the crude mixture was purified via column chromatography with silica gel eluting with hexane/ethyl acetate to give the title compound (22% yield). 1H NMR (CDCl3) δ 7.27-7.41 (m, 6H), 7.19 (t, 1H, J=2.5 Hz), 7.13 (d, 1H, J=2.3 Hz), 6.91 (dd, 1H, J=2.5, 8.8 Hz), 6.48 (m, 1H), 4.67 (s, 2H), 4.21 (m, 2H), 3.87 (m, 2H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe crude reaction
  3. filtrationThe reaction was filtrated over celite
  4. customthe crude mixture was purified via column chromatography with silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a0537e5de5884f2bb8522ffa3b0f0c7a
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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