Piperidine → HCID 67831574, compound

HRID 1030337Notes

Reaction equation

HRID 1030337 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7](I)[CH:8]=[CH:9][CH:10]=1)#[N:2].[F:12][C:13]1[CH:14]=[C:15]([O:28][CH2:29][C:30]#[CH:31])[CH:16]=[C:17]([C:19]2([O:26][CH3:27])[CH2:23][CH2:22][CH2:21][CH:20]2[O:24][CH3:25])[CH:18]=1.N1CCCCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:31]#[C:30][CH2:29][O:28][C:15]2[CH:16]=[C:17]([C:19]3([O:26][CH3:27])[CH2:23][CH2:22][CH2:21][CH:20]3[O:24][CH3:25])[CH:18]=[C:13]([F:12])[CH:14]=2)[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 18543430HCID 18543430, compoundHCID 19899549HCID 19899549, compound

Product 1

HCID 67831574HCID 67831574, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-cyanomethoxyphenyl iodide (0.355 g), tetrakis(triphenylphosphine)palladium (0.079 g) and toluene (7 ml) was stirred at ambient temperature for 15 minutes. To this mixture there were added in turn (1RS,2SR)-1-[5-fluoro-3-(2-propynyloxy)phenyl]-1,2-dimethoxycyclopentane (0.252 g), cuprous iodide (0.013 g) and piperidine (0.274 ml) and the mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between toluene and water. The organic layer was washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using methylene chloride as eluent. There was thus obtained (1RS,2SR)-1-[3-(3-(3-cyanomethoxyphenyl)prop-2-ynyloxy)-5-fluorophenyl-1,2-dimethoxycyclopentane (0.194 g, 35%), as an oil.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customThe mixture was partitioned between toluene and water
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-188095e44f0c4ec7ab05760ef9abd9aa
Source dataset
uspto-grants-1992_04
Patent number
US05105020

Reaction notes

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