(S)-(+)-4-(oxiranylmethoxy)benzo[b]furan → (2S)-1-(4-Benzo[b]furanoxy)-3-(4-(3-ethylbenzo[b]thiophen-2-yl)-piperidin-1-yl)-2-propanol Hydrate

HRID 1760620Notes

Reaction equation

HRID 1760620 reaction equation
[OH:1][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[CH:31]=[CH:30][O:29][C:28]=2[CH:27]=[CH:26][CH:25]=1>CO>[OH2:1].[O:29]1[CH:30]=[CH: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 20659907(S)-(+)-4-(oxiranylmethoxy)benzo[b]furanHCID 225958794-Hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine

Product 1

HCID 20751430(2S)-1-(4-Benzo[b]furanoxy)-3-(4-(3-ethylbenzo[b]thiophen-2-yl)-piperidin-1-yl)-2-propanol HydrateYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-hydroxy-4-(3-ethylbenzo[b]thiophen-2-yl)piperidine (0.067 g, 0.273 mmol) and (S)-(+)-4-(oxiranylmethoxy)benzo[b]-furan (0.052 g, 0.273 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/2% methanol in dichloromethane gradient elution) to give the final title compound as a yellow oil (0.049 g, 41%). FDMS m/e=436 (M++1). C26H29NO3S.0.75H2O

Workup

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

Sources & evidence

ORD record
ord-e8b30634e3704ef987f79943a8914e0c
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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