4-Pyrrolidinopyridine → HCID 57255840, compound

HRID 1609427Notes

Reaction equation

HRID 1609427 reaction equation
[Cl:1][C@@H:2]([CH3:20])[CH2:3][C@H:4]([CH3:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Cl:21][C@@H:22]([CH3:36])[CH2:23][C@H:24]([CH3:35])[O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1.N1(C2C=CN=CC=2)CCCC1>C(Cl)Cl>[Cl:1][C@@H:2]([CH3:20])[CH2:3][C@H:4]([CH3:19])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([O:25][C@@H:24]([CH3:35])[CH2:23][C@@H:22]([Cl:21])[CH3:36])=[CH:34][CH:33]=3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 755674-PyrrolidinopyridineHCID 18650833HCID 18650833, compoundHCID 18650843HCID 18650843, compound

Product 1

HCID 57255840HCID 57255840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.30 g of (S,S)-4-[4'-(3"-chloro-1"-methylbutoxy)phenyl]phenol, 0.24q of (S,S)-4-(3'-chloro-1'-methylbutoxy)benzoic acid, 0.22 g of dicyclocarbodiimide, 0.04 g of 4-pyrrolidinopyridine and 6 ml of methylene chloride were stirred together at room temperature for five hours. The dicyclohexyl urea thus precipitated was filtered and the filtrate was desolvated. The crude product thus obtained was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (4:1) as a developing solvent to thereby give 0.2 g of the title compound.

Workup

  1. customThe dicyclohexyl urea thus precipitated
  2. filtrationwas filtered
  3. customThe crude product thus obtained
  4. customwas purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (4:1) as a developing solvent

Sources & evidence

ORD record
ord-f7c32c06e6bc406da43115174ca86886
Source dataset
uspto-grants-1995_03
Patent number
US05401436

Reaction notes

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