4-(6-Fluoronaphth-2-yl)-1,2,5,6-tetrahydropyridine → (2S)-1-(4-Benzo[b]furanoxy)-3-(4-(6-fluoronaphth-2-yl)-1,2,5,6-tetrahydropyrid-1-yl)-2-propanol

HRID 1760623Notes

Reaction equation

HRID 1760623 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH:13]=1)[CH:6]=[CH:5]2.[O:18]1[CH2:20][C@H:19]1[CH2:21][O:22][C:23]1[C:31]2[CH:30]=[CH:29][O:28][C:27]=2[CH:26]=[CH:25][CH:24]=1>CO>[O:28]1[CH:29]=[CH:30][C:31]2[C:23]([O:22][CH2:21][C@@H:19]([OH:18])[CH2:20][N:15]3[CH2:16][CH2:17][C:12]([C:7]4[CH:6]=[CH:5][C:4]5[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=5)[CH:8]=4)=[CH:13][CH2:14]3)=[CH:24][CH:25]=[CH:26][C:27]1=2

Participants

4

Reactant 2

HCID 129927744-(6-Fluoronaphth-2-yl)-1,2,5,6-tetrahydropyridineHCID 20659907(S)-(+)-4-(oxiranylmethoxy)benzo[b]furan

Product 1

HCID 10158930(2S)-1-(4-Benzo[b]furanoxy)-3-(4-(6-fluoronaphth-2-yl)-1,2,5,6-tetrahydropyrid-1-yl)-2-propanolYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-(6-fluoronaphth-2-yl)-1,2,5,6-tetrahydropyridine (0.101 g, 0.444 mmol) and (S)-(+)-4-(oxiranylmethoxy)-benzo[b]furan (0.085 g, 0.444 mmol) in methanol (5 mL) was heated at reflux for 18 hours and then cooled and evaporated. The residue was purified by silica gel chromatography (dichloromethane/2% methanol in dichloromethane gradient elution) to give the title compound as a clear colorless oil (0.070 g, 38%). FDMS m/e=418 (M++1). C26H24FNO3.0.5H2O.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography (dichloromethane/2% methanol in dichloromethane gradient elution)

Sources & evidence

ORD record
ord-255c58723cec493cb5784605e135c0cd
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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