Conversion of indene to (1S)-amino-(2R)-indanol free of any stereoisomer, by combination of dioxygenase bioconversion and chemical steps

A process for synthesizing (1S)-amino-(2R)-indanol substantially free of any stereoisomer which comprises:

• (A) incubating a mixture comprising indene and Pseudomonas putida 421-5 (ATCC 55687) to give (1S,2R)-indandiol;
• (B) recovering the (1S,2R)-indandiol wherein said recovering comprises purifying the (1S,2R)-indandiol by chiral specific crystallization to obtain a (1S,2R)-indandiol substantially free of any stereoisomer;
• (C) dissolving one equivalent of the (1S,2R)-indandiol of step (B) in excess acetonitrile to give a second mixture, and maintaining the second mixture between about -40.degree. C. and about 25.degree. C.;
• (D) mixing thereto excess equivalents of strong acid;
• and
• (E) maintaining the reaction at between about -40.degree. C. and about 25.degree. C. to give (1S)-amino-(2R)-indanol substantially free of any stereoisomer.

A process for synthesizing (1S)-amino-(2R)-indanol substantially free of any stereoisomer which comprises:

• (A) incubating a mixture comprising indene and Pseudomonas putida F1(ATCC 55688) to give (1S,2R)-indandiol;
• (B) recovering the (1S,2R)-indandiol wherein said recovering comprises purifying the (1S,2R)-indandiol by chiral specific crystallization to obtain a (1S,2R)-indandiol substantially free of any stereoisomer;
• (C) dissolving one equivalent of the (1S,2R)-indandiol of step (B) in excess acetonitrile to give a second mixture, and maintaining the second mixture between about -40.degree. C. and about 25.degree. C.;
• (D) mixing thereto excess equivalents of strong acid;
• and
• (E) maintaining the reaction at between about -40.degree. C. and about 25.degree. C. to give (1S)-amino-(2R)-indanol substantially free of any stereoisomer.

A process for synthesizing (1S)-amino-(2R)-indanol substantially free of any stereoisomer which comprises:

• (A) incubating a mixture comprising indene and Rhodococcus B264-1 (ATCC 55806) to give (1S,2R)-indandiol;
• (B) recovering the (1S,2R)-indandiol wherein said recovering comprises purifying the (1S,2R)-indandiol by chiral specific crystallization to obtain a (1S,2R)-indandiol substantially free of any stereoisomer;
• (C) dissolving one equivalent of the (1S,2R)-indandiol of step (B) in excess acetonitrile to give a second mixture, and maintaining the second mixture between about -40.degree. C. and about 25.degree. C.;
• (D) mixing thereto excess equivalents of strong acid;
• and
• (E) maintaining the reaction at between about -40.degree. C. and about 25.degree. C. to give (1S)-amino-(2R)-indanol substantially free of any stereoisomer.