4-Hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine → (2S)-1-(2,3-Dihydro-4-benzo[b]furanoxy)-3-(4-(3-ethylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol

HRID 1760621Notes

Reaction equation

HRID 1760621 reaction equation
O[C:2]1([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:17][CH3:18])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:19]1[CH2:21][C@H:20]1[CH2:22][O:23][C:24]1[C:32]2[CH2:31][CH2:30][O:29][C:28]=2[CH:27]=[CH:26][CH:25]=1>CO>[O:29]1[CH2:30][CH2:31][C:32]2[C:24]([O:23][CH2:22][C@@H:20]([OH:19])[CH2:21][N:5]3[CH2:6][CH2:7][CH:2]([C:8]4[S:12][C:11]5[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=5[C:9]=4[CH2:17][CH3:18])[CH2:3][CH2:4]3)=[CH:25][CH:26]=[CH:27][C:28]1=2

Participants

4

Reactant 2

HCID 225958794-Hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidineHCID 86590503(S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan

Product 1

HCID 20751426(2S)-1-(2,3-Dihydro-4-benzo[b]furanoxy)-3-(4-(3-ethylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanolYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine (0.069 g, 0.281 mmol) and (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan (0.054 g, 0.281 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/1% methanol in dichloromethane) to give the title compound as a clear colorless oil (0.043 g, 35%). FDMS m/e=438 (M++1). C26H31NO3S.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-ce6569e440714a5d9cdd22045474a507
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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