Liladhar Murlidhar Waykole

Synthesis of Terfenadine Carboxylate

Abstract A synthesis of terfenadine carboxylate, 1, a metabolite of terfenadine 2, is described. In the key step, the sodium salt of 2-(4-bromophenyl)-2-methylpropionic acid, 7, was lithiated via a metal-halogen exchange using t-BuLi and subsequently condensed with 4-[4-(hydroxydiphenylmethylpiperidin-1-yl]butyraldehyde, 5, to afford terfenadine carboxylate, 1.

Amino Acids as a Chiral Pool: Synthesis of (S)‐and (R)‐2‐N‐Carbomethoxy‐5‐aminoindane from (S)‐ and (R)‐Phenylalanines

Abstract Enantioselective syntheses of (R)‐and (S)‐2‐N‐carbomethoxy‐5‐aminoindanes from (R)‐ and (S)‐phenylalanines, respectively, are described. A Friedel–Crafts reaction employing N‐carbomethoxy phenylalanine leads to chiral 2‐N‐carbomethoxy‐1‐indanone, which is diastereoselectively reduced to 1‐hydroxy‐2‐N‐carbomethoxyindane. After protection of the hydroxyl group, a regioselective nitration gives a 6‐nitroindane intermediate, which upon hydrogenation affords (R)‐or (S)‐2‐N‐carbomethoxy‐5‐aminoindane.

Opening of Glycidol with Phenols in Water Using Catalytic Amounts of Sodium Hydroxide: A Practical Synthesis of 3-Aryloxy-1,2-propanediols

Abstract A practical synthesis of enantiopure 3-aryloxy-1,2-propanediols by opening of (S)-glycidol with phenols under aqueous conditions using catalytic amounts of sodium hydroxide is described.

Practical Synthesis of Diaryloxymethanes

Abstract Diaryloxymethanes were prepared by treating phenols with sodium hydride and dichloromethane in N-methyl-pyrrolidinone (NMP) at 40°C.

Selective Benzylic Bromination of 2-Methylnaphthalene

Abstract A practical synthesis of 2-(bromomethyl)naphthalene (1), by selective benzylic bromination of 2-methylnaphthalene (2), with bromine in heptane in the presence of lanthanum acetate hydrate is described.