trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

HRID 1377758Notes

Reaction equation

HRID 1377758 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][N:17](CC4C=CC=CC=4)[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)=O.CO.[Pd]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 70091886trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine

Product 1

HCID 70093357trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidineYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent2×

Procedure

trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine (3.5 g, 8.6 mmol) was dissolved in 20 mL of 4% HCO2H:methanol. While stirring at room temperature, 10% Pd/C (450 mg) was added in small portions. After several hours the reaction was diluted with methanol. Filtration through Celite followed by concentration under reduced pressure yielded a yellow oil residue. This residue was partitioned between CH2Cl2 and sat. NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, dried (K2CO3), filtered, and concentrated under reduced pressure to afford a pale oil. Chromatography on silica gel (8:1:1, CH2Cl2 :ethyl acetate:methanol) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine as a colorless oil (2.3 g, 84%). 1H-NMR (300 MHz): δ 2.86-3.04 (m, 2), 3.29-3.52 (m, 4), 3.68 (s, 3), 3.83 (s, 3).

Workup

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration under reduced pressure
  3. customyielded a yellow oil residue
  4. customThis residue was partitioned between CH2Cl2 and sat. NaHCO3
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  7. dry with materialdried (K2CO3)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a pale oil

Sources & evidence

ORD record
ord-bfba3adc4929448092eb0adfb87e29b7
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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