Sodium methanethiolate → tert-Butyl 4-((methylthio)methyl)piperidine-1-carboxylate

HRID 1894361Notes

Reaction equation

HRID 1894361 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][S-:27].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][S:27][CH3:26])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidine

Product 1

HCID 21087276tert-Butyl 4-((methylthio)methyl)piperidine-1-carboxylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (9.765 g, 26.43 mmol) in methanol (1 00mL) at room temperature was added sodium thiomethoxide (5.557 g, 79.29 mmol, Aldrich). The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was taken in methylene chloride and washed with water (3×) and brine (1×). The organic layer was dried over anhydrous sodium sulfate and concentrated to give a clear oil as crude product of 4-methylsulfanylmethyl-piperidine-1-carboxylic acid tert-butyl ester (6.37 g).

Workup

  1. concentrationthen concentrated
  2. washwashed with water (3×) and brine (1×)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-417ca69b37364c94ae112a5df2ac1c7c
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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