1,1'-Carbonyldiimidazole → HCID 44302614, compound

HRID 1377768Notes

Reaction equation

HRID 1377768 reaction equation
[C:1]([C@H:4]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)[CH2:7][N:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:5]1)(O)=[O:2].C(N1C=CN=C1)([N:29]1C=CN=C1)=O>C(Cl)Cl>[NH2:29][C:1]([C@H:4]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)[CH2:7][N:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:5]1)=[O:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 44302395HCID 44302395, compound

Product 1

HCID 44302614HCID 44302614, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-3-carboxy-4-(3-cyclopentoxy-4-methoxyphenyl)-1-(methoxycarbonyl)pyrrolidine (1.5 g, 4.1 mmol) in 11 mL of CH2Cl2 at 0° C. was added 1,1'-carbonyldiimidazole (736 mg, 4.5 mmol) in portions. The cooling bath was removed, and the solution was stirred at room temperature for 20 min. Ammonia gas was passed over the stirring solution for 4 min, and stirring was continued an additional 15 min. The solution was diluted with CH2Cl2 and poured into 1M H3PO4. The aqueous layer was extracted with CH2Cl2 (2×), and the combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to a pale yellow foam. Silica gel chromatography (8:1:1, CH2Cl2 :ethyl acetate:methanol) provided trans-3-aminocarbonyl-4-(3-cyclopentoxy-4-methoxyphenyl)-I-(methoxycarbonyl)pyrrolidine as a white solid (1.1 g, 76%), m.p. 130°-32° C. Anal. Calcd for C19H26N2O5 : C, 62.97; H, 7.23; N, 7.73. Found: C, 63.03; H, 7.28; N, 7.65.

Workup

  1. customThe cooling bath was removed
  2. waitAmmonia gas was passed over the stirring solution for 4 min
  3. stirringstirring
  4. waitwas continued an additional 15 min
  5. additionThe solution was diluted with CH2Cl2
  6. additionpoured into 1M H3PO4
  7. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure to a pale yellow foam

Sources & evidence

ORD record
ord-9e90f56cb9ae418f81364c0a38f53614
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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