Pyrrolidine → HCID 18781976, compound

HRID 1420544Notes

Reaction equation

HRID 1420544 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:32])[CH2:16][N:17]2[CH:20]([S:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC=C)=[O:26])[CH2:19][C:18]2=[O:31])=[CH:4][CH:3]=1.N1CCCC1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:32])[CH2:16][N:17]2[CH:20]([S:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH2:19][C:18]2=[O:31])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 18782043HCID 18782043, compound

Product 1

HCID 18781976HCID 18781976, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[6-(4-Fluorophenyl)hexyl]-[4-(3-allyloxycarbonylpropyl)thio-2-oxo-azetidin-1-yl]-acetamide (1.4 g) was dissolved in dry dichloromethane (30 ml) and the resulting solution treated with pyrrolidine (0.3 g) and (tetrakistriphenylphosphino)palladium (0.2 g) at room temperature until TLC analysis showed absence of starting material. The mixture was washed with dilute HCl, brine, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (dichloromethane:methanol:acetic acid, 90:9:1) to give the title compound as an oil, 0.7 g, 52% yield.

Workup

  1. washThe mixture was washed with dilute HCl, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol:acetic acid, 90:9:1)

Sources & evidence

ORD record
ord-1153ff43031241679c93be0cb72c2310
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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