S-[[1-(cyanomethyl)cyclopropyl]methyl] ethanethioate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the nitrile of Step 8 (45 g, 266 mmol) in MeOH (1.36 L) was added H2O(84 mL) and conc. H2SO4 (168 mL). The mixture was heated to reflux for 20 hr, cooled to 25° C., H2O(1 L) was added and the product was extracted with CH2Cl2 (2×1.5 L). The organic extract was washed with H2O and dried over Na2SO4. Concentration of the organic solution gave 36 g (93%) of the title compound. The mixture was heated to reflux for 20 hr the product was extracted with CH2Cl2 (2×1.5 L) The organic extract was washed with H2O dried over Na2SO4

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the nitrile of Step 8 (45 g, 266 mmol) in MeOH (1.36 L) was added H2O(84 mL) and conc. H2SO4 (168 mL). The mixture was heated to reflux for 20 hr, cooled to 25° C., H2O(1 L) was added and the product was extracted with CH2Cl2 (2×1.5 L). The organic extract was washed with H2O and dried over Na2SO4. Concentration of the organic solution gave 36 g (93%) of the title compound. The mixture was heated to reflux for 20 hr the product was extracted with CH2Cl2 (2×1.5 L) The organic extract was washed with H2O dried over Na2SO4

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The first step comprises converting the starting material 1,1-cyclopropanedimethanol II into the corresponding cyclic sulfite III by using thionyl chloride and in the presence of a base such as diisopropylethylamine. The cyclic sulfite III is treated with catalytic amount of sodium iodide and sodium cyanide to obtain the compound 1-(hydroxymethyl)cyclopropaneacetonitrile IV, which is converted into the corresponding mesylate 1-(methanesulfonyloxymethyl)-cyclopropaneacetonitrile V, by using methanesulfonyl chloride in the presence of a base. Compound V is treated with potassium thioacetate or thioacetic acid in the presence of a base to yield the compound 1-(acetylthiomethyl)-cyclopropaneacetonitrile VI. In the last step, compound VI is converted into 1-(mercaptomethyl)cyclopropaneacetic acid VII by reacting compound VI in a biphasic solvent system comprising toluene and aqueous NaOH for 16-18 hours.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the nitrile of Step 8 (45 g, 266 mmol) in MeOH (1.36 L) was added H2O (84 mL) and cone. H2SO4 (168 mL). The mixture was heated to reflux for 20 hours, cooled to 25° C., H2O (1 L) was added and the product was extracted with CH2Cl2 (2×1.5 L). The organic extract was washed with H2O and dried over Na2SO4. Concentration of the organic solution gave 36 g (93%) of the title compound. The mixture was heated to reflux for 20 hours the product was extracted with CH2Cl2 (2×1.5 L) The organic extract was washed with H2O dried over Na2SO4