The present invention relates to a short enantioselective synthesis of 1-amino aryl tetraline compounds of Formula 1 via nucleophilic enamine catalysis using organocatalyst such as proline.

##STR00001## wherein R.sub.1 and R.sub.2 represent independent of each other hydrogen, (un)substituted or substituted amine; R.sub.3 and R.sub.4 represent independent of each other hydrogen or halogen.

A method for producing meta-xylylenediisocyanates includes a reaction step in which monohalogenated benzenes, formaldehydes, and an amide compound represented by general formula (1) below are allowed to react in the presence of an acidic liquid to produce a bisamide compound; a dehalogenation step in which in the bisamide compound, the halogen atom derived from the monohalogenated benzenes is replaced with a hydrogen atom; and a thermal decomposition step in which the bisamide compound from which the halogen atom is eliminated is subjected to thermal decomposition. In the reaction step, the acidic liquid contains inorganic acid, the equivalent ratio of the hydrogen atom of the inorganic acid relative to the monohalogenated benzenes is more than 14, the acidic liquid has an inorganic acid concentration of more than 90 mass %, and the reaction temperature is more than 10 C. General formula (1): ##STR00001##
wherein R.sup.1 represents an alkoxy group or an amino group.

A method for producing meta-xylylenediisocyanates includes a reaction step in which monohalogenated benzenes, formaldehydes, and an amide compound represented by general formula (1) below are allowed to react in the presence of an acidic liquid to produce a bisamide compound; a dehalogenation step in which in the bisamide compound, the halogen atom derived from the monohalogenated benzenes is replaced with a hydrogen atom; and a thermal decomposition step in which the bisamide compound from which the halogen atom is eliminated is subjected to thermal decomposition. In the reaction step, the acidic liquid contains inorganic acid, the equivalent ratio of the hydrogen atom of the inorganic acid relative to the monohalogenated benzenes is more than 14, the acidic liquid has an inorganic acid concentration of more than 90 mass %, and the reaction temperature is more than 10 C. General formula (1): ##STR00001##
wherein R.sup.1 represents an alkoxy group or an amino group.

A sacubitril intermediate, a preparation method therefor, and use thereof. A key intermediate N-Boc amino alcohol represented by formula (10) or formula (10-a) can be efficiently prepared. The intermediate can be used to prepare a neutral endopeptidase (NEP) inhibitor or a prodrug thereof, particularly a NEP inhibitor comprising a skeleton of -amino--biphenyl--methylalkanoic acid or ester, such as sacubitril. Also provided are intermediates for preparing formula (10) or formula (10-a). Raw materials of the process route are cheap, the operation is simple and convenient, the production cost is low, and the method is suitable for industrial production

##STR00001##

A sacubitril intermediate, a preparation method therefor, and use thereof. A key intermediate N-Boc amino alcohol represented by formula (10) or formula (10-a) can be efficiently prepared. The intermediate can be used to prepare a neutral endopeptidase (NEP) inhibitor or a prodrug thereof, particularly a NEP inhibitor comprising a skeleton of -amino--biphenyl--methylalkanoic acid or ester, such as sacubitril. Also provided are intermediates for preparing formula (10) or formula (10-a). Raw materials of the process route are cheap, the operation is simple and convenient, the production cost is low, and the method is suitable for industrial production

##STR00001##

This document discloses molecules having the following formula (Formula One): ##STR00001##
and processes associated therewith.

This document discloses molecules having the following formula (Formula One): ##STR00001##
and processes associated therewith.

This document discloses molecules having the following formula (Formula One): ##STR00001##
and processes associated therewith.

This document discloses molecules having the following formula (Formula One): ##STR00001##
and processes associated therewith.

This document discloses molecules having the following formula (Formula One): ##STR00001##
and processes associated therewith.