(S)-(+)-4-(oxiranylmethoxy)benzo[b]thiophene → (2S)-(-)-1-(4-Benzo[b]thiophenoxy)-3-(4-(6-fluoronaphth-2-yl)Piperidin-1-yl)-2-propanol

HRID 1837485Notes

Reaction equation

HRID 1837485 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:31]2[CH:30]=[CH:29][S:28][C:27]=2[CH:26]=[CH:25][CH:24]=1>CO>[S: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[CH2:14][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)=[CH:24][CH:25]=[CH:26][C:27]1=2

Participants

4

Reactant 2

HCID 12992768(S)-(+)-4-(oxiranylmethoxy)benzo[b]thiopheneHCID 129927764-(6-Fluoronaphth-2-yl)piperidine

Product 1

HCID 12992777(2S)-(-)-1-(4-Benzo[b]thiophenoxy)-3-(4-(6-fluoronaphth-2-yl)Piperidin-1-yl)-2-propanolYield 50.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-(6-fluoronaphth-2-yl)piperidine (0.069 g, 0.301 mmol) and (S)-(+)-4-(oxiranylmethoxy)benzo[b]thiophene (0.062 g, 0.301 mmol) in methanol (3 mL) was heated at reflux 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 (0.066 g, 50%). FDMS m/e 436 (M++1). C26H26FNO2S.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was purified
  5. washsilica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient elution)

Sources & evidence

ORD record
ord-b7166090fccc411d84dfb35527a30526
Source dataset
uspto-grants-2004_08
Patent number
US06784180B2

Reaction notes

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