Potassium Iodide → methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylate

HRID 2186362Notes

Reaction equation

HRID 2186362 reaction equation
[OH:1][CH:2]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][NH:8][CH2:7][C@@H:6]1[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:35](Br)[C:36]#[CH:37]>C(#N)C>[OH:1][CH:2]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:37][C:36]#[CH:35])[CH2:7][C@@H:6]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 66688355HCID 66688355, compound

Product 1

HCID 131723275methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 2.45 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate, 2.1 g of potassium carbonate, 0.95 g of potassium iodide, and 0.6 cm3 of propargyl bromide in 50 cm3 of acetonitrile was stirred for 40 hours at a temperature in the region of 20° C. in an inert atmosphere. After filtering the reaction mass, the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography on a column of silica gel (particle size 20-45 μm; diameter 2.5 cm; mass 50 g), elution was carried out with ethyl acetate, and 60-cm3 fractions were collected. Fractions 6 to 12 were combined and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 1.35 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylate were obtained in the form of a gum.

Workup

  1. filtrationAfter filtering the reaction mass
  2. customthe filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  3. customThe residue obtained
  4. customwas purified by chromatography on a column of silica gel (particle size 20-45 μm; diameter 2.5 cm; mass 50 g), elution
  5. customwere collected
  6. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-aea98fbe24e14caf92e767b3de394c53
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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