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

HRID 422165Notes

Reaction equation

HRID 422165 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f5667bb181a641d89ca713d9bfc549c5
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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