Pyrrolidine → (1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine

Participants

Reaction Steps

4 g of (3aS,cis) hexahydro-1-(3H)-isobenzofuranone in 20 ml of methanol and 4.76 ml of pyrrolidine with 0.386 g of sodium methylate were refluxed for 20 hours and one half of the methanol was distilled off at 50° C. under reduced pressure. Water and ice were added and the pH was adjusted to 1 by adding 2N hydrochloric acid. Extraction was done with methylene chloride and the extracts were washed with water, dried, filtered, evaporated to dryness under reduced pressure and crystallized from isopropyl ether to obtain 3.89 g of (1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine melting at 115° C.

Provenance & Evidence