Cesium carbonate → (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

HRID 422165노트

반응식

HRID 422165 반응식
CS(O[CH2:6][C@@H:7]1[C@:16]2([CH3:17])[C@H:11]([C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9][C@:8]1([OH:21])[CH3:20])(=O)=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([SH:30])[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([S:30][CH2:6][C@@H:7]2[C@:16]3([CH3:17])[C@H:11]([C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15]3)[CH2:10][CH2:9][C@@:8]2([CH3:20])[OH:21])[CH:27]=[CH:28][CH:29]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 849893-MethoxybenzenethiolHCID 58294786((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate

생성물 1

HCID 58294805(1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol수율 71%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of [(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]methyl methanesulfonate (12) (5.0 g, 16 mmol), 3-methoxybenzenethiol (1.9 mL, 16 mmol), cesium carbonate (15.3 g, 47.2 mmol) in anhydrous CH3CN (200 mL) was prepared under N2. The mixture was heated to reflux and stirred for 18 h. The reaction mixture was filtered and the filtrate concentrated to dryness. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1) to yield (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (13-1) (4.0 g, 71% yield) as a yellow oil.

후처리

  1. customwas prepared under N2
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate concentrated to dryness
  6. customThe crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1)

출처 및 근거

ORD 기록
ord-f5667bb181a641d89ca713d9bfc549c5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101605B2

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