2-(3,4-dihydro-2H-chromen-4-yl)acetonitrile

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The saturated cyano compound obtained in Step B is solubilised in the reactor of a Parr apparatus with acetic anhydride. Sodium acetate (1.5 eq.) and also Raney nickel (6 mg per 50 mg of product) are then introduced into the reaction medium. The whole is heated at 50° C. under hydrogen pressure of 40 psi for 12 hours. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction is carried out with ethyl acetate. Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3) results in the desired amide. Colourless gum. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3)

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

Procedure: The unsaturated compound obtained in Step A (Z+E mixture), solubilised in ethanol (20 ml), is introduced into the reactor of a Parr apparatus. 10% (by weight) palladium-on-carbon is then added. The double bond is hydrogenated at a pressure of 45 psi for 12 hours. The catalyst is removed by filtration; the solvent is then evaporated. The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7. Colourless oil. The catalyst is removed by filtration the solvent is then evaporated The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The saturated cyano compound obtained in Step B is solubilized in the reactor of a Parr apparatus with acetic anhydride. Sodium acetate (1.5 eq.) and also Raney nickel (6 mg per 50 mg of product) are then introduced into the reaction medium. The whole is heated at 50° C. under hydrogen pressure of 40 psi for 12 hours. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction is carried out with ethyl acetate. Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3) results in the desired amide. Colourless gum. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3)

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

Procedure: The unsaturated compound obtained in Step A (Z+E mixture), solubilized in ethanol (20 ml), is introduced into the reactor of a Parr apparatus. 10% (by weight) palladium-on-carbon is then added. The double bond is hydrogenated at a pressure of 45 psi for 12 hours. is introduced into the reactor of a Parr apparatus

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The saturated cyano compound obtained in Step B is solubilised in the reactor of a Parr apparatus with acetic anhydride. Sodium acetate (1.5 eq.) and also Raney nickel (6 mg per 50 mg of product) are then introduced into the reaction medium. The whole is heated at 50° C. under hydrogen pressure of 40 psi for 12 hours. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction is carried out with ethyl acetate. Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3) results in the desired amide. Colourless gum. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3)

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

Procedure: The unsaturated compound obtained in Step A (Z+E mixture), solubilised in ethanol (20 ml), is introduced into the reactor of a Parr apparatus. 10% (by weight) palladium-on-carbon is then added. The double bond is hydrogenated at a pressure of 45 psi for 12 hours. The catalyst is removed by filtration; the solvent is then evaporated. The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7. Colourless oil. The catalyst is removed by filtration the solvent is then evaporated The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The saturated cyano compound obtained in Step B is solubilized in the reactor of a Parr apparatus with acetic anhydride. Sodium acetate (1.5 eq.) and also Raney nickel (6 mg per 50 mg of product) are then introduced into the reaction medium. The whole is heated at 50° C. under hydrogen pressure of 40 psi for 12 hours. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction is carried out with ethyl acetate. Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3) results in the desired amide. Colourless gum. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3)

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

Procedure: The unsaturated compound obtained in Step A (Z+E mixture), solubilized in ethanol (20 ml), is introduced into the reactor of a Parr apparatus. 10% (by weight) palladium-on-carbon is then added. The double bond is hydrogenated at a pressure of 45 psi for 12 hours. is introduced into the reactor of a Parr apparatus

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The saturated cyano compound obtained in Step B is solubilised in the reactor of a Parr apparatus with acetic anhydride. Sodium acetate (1.5 eq.) and also Raney nickel (6 mg per 50 mg of product) are then introduced into the reaction medium. The whole is heated at 50° C. under hydrogen pressure of 40 psi for 12 hours. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction is carried out with ethyl acetate. Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3) results in the desired amide. Colourless gum. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3)

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

Procedure: The unsaturated compound obtained in Step A (Z+E mixture), solubilised in ethanol (20 ml), is introduced into the reactor of a Parr apparatus. 10% (by weight) palladium-on-carbon is then added. The double bond is hydrogenated at a pressure of 45 psi for 12 hours. The catalyst is removed by filtration; the solvent is then evaporated. The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7. Colourless oil. The catalyst is removed by filtration the solvent is then evaporated The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7