Diethyl Ether → Tert-butyl 3-cyclohexyl-3-[(methylthio)methyl]-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1178897Notes

Reaction equation

HRID 1178897 reaction equation
[CH:1]1([C:7]2([CH2:22]OS(C)(=O)=O)[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][S-:29].[Na+].C(OCC)C>CN(C=O)C>[CH:1]1([C:7]2([CH2:22][S:29][CH3:28])[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4378561Sodium methanethiolateHCID 86607399Tert-butyl 3-cyclohexyl-3-{[(methylsulfonyl)oxy]methyl}-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 58695800Tert-butyl 3-cyclohexyl-3-[(methylthio)methyl]-8-azabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 3-cyclohexyl-3-{[(methylsulfonyl)oxy]methyl}-8-azabicyclo[3.2.1]octane-8-carboxylate (3-4) (1.01 g, 2.69 mmol) in 50 mL of DMF was added sodium thiomethoxide (0.943 g, 13.5 mmol). The mixture was stirred at 60° C. for 3 days. After cooling to room temperature, 200 mL of diethyl ether was added. The solid was filtered and the filtrates were washed with water three times. The organics were dried over anhydrous MgSO4, filtered, and concentrated to give (3-5) as a clear yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solid was filtered
  3. washthe filtrates were washed with water three times
  4. dry with materialThe organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-00e912ccc32541879778f428edb28df7
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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