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

HRID 1760630노트

반응식

HRID 1760630 반응식
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

참가 물질

4

반응물 3

HCID 887MethanolHCID 20659907(S)-(+)-4-(oxiranylmethoxy)benzo[b]furanHCID 225958521-(t-Butyloxycarbonyl)-4-(4-methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-61958b1e7e134f83b2c7d611609910fa
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844344B2

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