Methanol → trans-(2S)-1-(4-Benzo[b]furanoxy)-3-(2-methyl-4-(4-methylbenzothiazol-2-yl)piperidin-1-yl)-2-propanol Oxalate

HRID 1760630Notes

Reaction equation

C([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=3[N:18]=2)=[CH:10][CH:9]1[CH3:24])=[O:7])(C)(C)C.[O:25]1[CH2:27][C@H:26]1[CH2:28][O:29][C:30]1[C:38]2[CH:37]=[CH:36][O:35][C:34]=2[CH:33]=[CH:32][CH:31]=1.C[OH:40]>>[C:36]([OH:35])(=[O:40])[C:6]([OH:5])=[O:7].[O:35]1[CH:36]=[CH:37][C:38]2[C:30]([O:29][CH2:28][C@@H:26]([OH:25])[CH2:27][N:8]3[CH2:13][CH2:12][C@@H:11]([C:14]4[S:15][C:16]5[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=5[N:18]=4)[CH2:10][C@@H:9]3[CH3:24])=[CH:31][CH:32]=[CH:33][C:34]1=2

Participants

Reactant 3

HCID 887Methanol

HCID 20659907(S)-(+)-4-(oxiranylmethoxy)benzo[b]furan

HCID 225958521-(t-Butyloxycarbonyl)-4-(4-methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine

Product 1

HCID 69739947trans-(2S)-1-(4-Benzo[b]furanoxy)-3-(2-methyl-4-(4-methylbenzothiazol-2-yl)piperidin-1-yl)-2-propanol Oxalate

Procedure

A solution of trans-4-(4-methylbenzothiazol-2-yl)-2-methylpiperidine (0.061 g, 0.248 mmol, prepared in example 24) and (S)-(+)-4-(oxiranylmethoxy)benzo[b]furan (0.047 g, 0.248 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/0.2% ammonium hydroxide in dichloromethane gradient elution) to give the free bases of the title compounds as two separate yellow oils. The oxalate salts were prepared to give the title compounds.

Workup

temperatureat reflux for 18 hours
temperaturecooled
customevaporated
customThe residue was purified
washsilica gel chromatography (dichloromethane/2% methanol/0.2% ammonium hydroxide in dichloromethane gradient elution)

Sources & evidence

ORD record: ord-61958b1e7e134f83b2c7d611609910fa
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844344B2

Reaction notes

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