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

HRID 422154Notes

Reaction equation

HRID 422154 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.CS(O[CH2:15][C@@H:16]1[C@:25]2([CH3:26])[C@H:20]([C:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18][C@:17]1([OH:30])[CH3:29])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:15][C@@H:16]2[C@:25]3([CH3:26])[C@H:20]([C:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][CH2:24]3)[CH2:19][CH2:18][C@@:17]2([CH3:29])[OH:30])[CH:6]=[CH:7][CH:8]=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 74.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methoxythiophenol (2.20 g, 15.7 mmol), [(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]methyl methanesulfonate (12) (5.0 g, 15 mmol), and Cs2CO3 (15.30 g, 47.16 mmol) in CH3CN (600 mL) was stirred at room temperature for 1 h, then refluxed for 24 h. After cooling, the mixture was concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 10:1 to 6:1) to give (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (13-1) (4.03 g, 71%) as a yellow oil.

Workup

  1. temperaturerefluxed for 24 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. custompurified by column chromatography on silica gel (Hexanes/EtOAc, 10:1 to 6:1)

Sources & evidence

ORD record
ord-b403f64b4eaf489e9fc93e9b7f1a7281
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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