Sodium methanethiolate → HCID 67197589, compound

HRID 547804Notes

Reaction equation

HRID 547804 reaction equation
[CH3:1][S-:2].[Na+].[CH2:4]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19]OS(C)(=O)=O)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[CH2:4]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][S:2][CH3:1])=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 18375727HCID 18375727, compound

Product 1

HCID 67197589HCID 67197589, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 1.81 g (25.8 mmol) sodium methanethiolate in 25 ml methanol was added a solution of 1.35 g (4.31 mmol) 2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid benzyl ester in 25 ml methanol. Conversion was monitored by thin layer chromatography. After complete consumption of the starting material the reaction mixture was diluted with ethyl acetate and washed with two portions of water. The organic layer was dried over sodium sulfate. Flash chromatography gave 0.89 g (3.4 mmol, 78%) (S)-2-methylsulfanylmethyl-pyrrolidine-1-carboxylic acid benzyl ester as a light yellow oil.

Workup

  1. customAfter complete consumption of the starting material the reaction mixture
  2. additionwas diluted with ethyl acetate
  3. washwashed with two portions of water
  4. dry with materialThe organic layer was dried over sodium sulfate

Sources & evidence

ORD record
ord-270f2c3b6c30472c8e77b2b6a85a812f
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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