4-Hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidine → (2S)-(-)-1-(4-Benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol Hemihydrate

HRID 1760618Notes

Reaction equation

HRID 1760618 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[CH3:17])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[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>[OH2:1].[O:28]1[CH:29]=[CH:30][C:31]2[C:23]([O:22][CH2:21][C@@H:19]([OH:18])[CH2:20][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[CH3:17])[CH2:3][CH2:4]3)=[CH:24][CH:25]=[CH:26][C:27]1=2.[O:28]1[CH:29]=[CH:30][C:31]2[C:23]([O:22][CH2:21][C@@H:19]([OH:18])[CH2:20][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[CH3:17])[CH2:3][CH2:4]3)=[CH:24][CH:25]=[CH:26][C:27]1=2

Participants

4

Reactant 2

HCID 129927674-Hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidineHCID 20659907(S)-(+)-4-(oxiranylmethoxy)benzo[b]furan

Product 1

HCID 131724711(2S)-(-)-1-(4-Benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol HemihydrateYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidine (0.074 g, 0.320 mmol) and (S)-(+)-4-(oxiranylmethoxy)-benzo[b]furan (0.061 g, 0.320 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 gradient elution) to give the final title compound as a clear colorless oil (0.057 g, 42%). FDMS m/e=422 (M++1). C25H27NO3S.0.5H2O

Workup

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

Sources & evidence

ORD record
ord-72af28151ba8439e93e5576d7553f880
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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