Process for producing optically active cyclobutylamines

Details Process for producing optically active cyclobutylamines Process for producing optically active cyclobutylamines

1991-09-10

1992-11-24

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

556413, 560106, 560252, 564303, 564304, C07C 6974

Patent

active

051663970

ABSTRACT:
This invention relates to a process for producing an optically active cyclobutylamine which comprises reacting a racemic modification of cyclobuthylamine represented by the following general formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 represent each a hydrogen atom or a protecting group; with an optically active N-acylphenylglycine to thereby give two corresponding diastereomeric salts, crystallizing the more difficultly soluble diastereomeric salt and isolating the corresponding optically active cyclobutylamine from the diastereomeric salt thus crystallized. The optically active substances of the compound of the above general formula [I] are useful as, for example, an intermediate in the synthesis of 9-[(1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutyl]guanine which is expected as an antiviral agent.

REFERENCES:
patent: 5057535 (1991-10-01), Shiozawa
Morrison, "Organic Chemistry," 3rd Ed, pp. 235-237 (1973).
Suzuki, Chem. Abstr. 80:133826x (1974).
Furuta, Chem. Abstr. 89:109128m (1978).
Shiozawa, Chem. Abstr. 109:128823g (1988).
Koshigoe, Chem. Abstr. 112:7918v (Jan. 1, 1990).
Sugimura, Chem. Abstr. 112:20894d (Jan. 15, 1990).

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