(S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan → (2s)-(-)-1-(2,3-Dihydro-4-benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol oxalate

HRID 1760619Notes

Reaction equation

HRID 1760619 reaction equation
[OH2:1].O1C=CC2C([O:11][CH2:12][C@@H:13]([OH:31])CN3CCC(C4SC5C=CC=CC=5C=4C)CC3)=CC=CC1=2.[O:32]1[CH:36]=[CH:35][C:34]2[C:37]([O:41][CH2:42][C@@H:43]([OH:61])[CH2:44][N:45]3[CH2:50][CH2:49][CH:48]([C:51]4[S:55][C:54]5[CH:56]=[CH:57][CH:58]=[CH:59][C:53]=5[C:52]=4[CH3:60])[CH2:47][CH2:46]3)=[CH:38][CH:39]=[CH:40][C:33]1=2.O1C[C@H]1COC1C2CCOC=2C=CC=1>CO>[C:13]([OH:31])(=[O:32])[C:12]([OH:11])=[O:1].[O:32]1[CH2:36][CH2:35][C:34]2[C:37]([O:41][CH2:42][C@@H:43]([OH:61])[CH2:44][N:45]3[CH2:46][CH2:47][CH:48]([C:51]4[S:55][C:54]5[CH:56]=[CH:57][CH:58]=[CH:59][C:53]=5[C:52]=4[CH3:60])[CH2:49][CH2:50]3)=[CH:38][CH:39]=[CH:40][C:33]1=2

Participants

4

Reactant 2

HCID 86590503(S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furanHCID 131724711(2S)-(-)-1-(4-Benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol Hemihydrate

Product 1

HCID 20751427(2s)-(-)-1-(2,3-Dihydro-4-benzo[b]furanoxy)-3-(4-(3-methylbenzo[b]thiophen-2-yl)piperidin-1-yl)-2-propanol oxalateYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution 4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)piperidine (0.070 g, 0.303 mmol, prepared in example 11) and (S)-(+)-4-(oxiranylmethoxy)-2,3-dihydrobenzo[b]furan (0.058 g, 0.303 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 free base of the title compound as a clear colorless oil (0.067 g, 52%). The oxalate salt was prepared to give the title compound. FDMS, m/e=424 (M++1 of free base). [α]D=−9.09 (c=0.44, methanol). C25H29NO3S.C2H2O4

Workup

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

Sources & evidence

ORD record
ord-c00dadd134fa483a8c95aa18b739b25b
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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