4-(6-Fluoronaphth-2-yl)piperidine → (2S)-(+)-1-(7-Benzo[b]furanoxy)-3-(4-(6-fluoronaphth-2-yl)-piperidin-1-yl)-2-propanol Hydrate

HRID 1760626Notes

Reaction equation

HRID 1760626 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[CH:6]=[CH:5]2.[O:18]1[CH2:20][C@H:19]1[CH2:21][O:22][C:23]1[C:28]2[O:29][CH:30]=[CH:31][C:27]=2[CH:26]=[CH:25][CH:24]=1>CO>[OH2:18].[O:29]1[CH:30]=[CH:31][C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([O:22][CH2:21][C@@H:19]([OH:18])[CH2:20][N:15]3[CH2:14][CH2:13][CH: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)[CH2:17][CH2:16]3)[C:28]1=2

Participants

4

Reactant 2

HCID 129927764-(6-Fluoronaphth-2-yl)piperidineHCID 86590504(S)-(+)-7-(oxiranylmethoxy)-benzo[b]furan

Product 1

HCID 20751433(2S)-(+)-1-(7-Benzo[b]furanoxy)-3-(4-(6-fluoronaphth-2-yl)-piperidin-1-yl)-2-propanol Hydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-(2-(6-fluoro)naphthyl)piperidine (0.0692 g, 0.302 mmol, prepared in example 19) and (S)-(+)-7-(oxiranylmethoxy)-benzo[b]furan (0.0574 g, 0.302 mmol) in methanol (3 mL) was refluxed for 18 hours and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient elution) to give the title compound as a white amorphous solid (0.067 g, 53%). FDMS m/e=420 (M++1). [α]D=2.14 (c 0.467, methanol). C26H26NO3F.0.2H2O

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was purified
  4. washsilica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient elution)

Sources & evidence

ORD record
ord-c42f713700344b01a572a6315f22d778
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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