Chemo-enzymatic synthesis of all four diastereoisomers of 1-fluoro-2-amino-indane

The four diastereoisomers of 1-fluoro-2-amino-indane have been synthesized in high enantiomeric excess with lipase resolution of cis-2-azido-1-indanol as a key step.

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(1S,2R)-1-Fluoro-2-amino-indane hydrochloride saltC9ClH11NEe = 99%[α]D20=+18.3 (c 0.34, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1S,2R)

(1R,2S)-1-Fluoro-2-amino-indane hydrochloride saltC9ClH11NEe = 99%[α]D20=-18.6 (c 0.47, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1R,2S)

(1R,2R)-1-Fluoro-2-amino-indane hydrochloride saltC9ClH11NEe = 99%[α]D20=+19.3 (c 1, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1R,2R)

(1S,2S)-1-Fluoro-2-amino-indane hydrochloride saltC9ClH11NEe = 99%[α]D20=-19.5 (c 1, MeOH)Source of chirality: enzymatic resolutionAbsolute configuration: (1S,2S)