‘Easy-on, easy-off’ resolution of chiral 1-phenylethylamine catalyzed by Candida antarctica lipase B

An ‘easy-on, easy-off’ process for the effective resolution of (±)-1-phenylethylamine was designed using the lipase B of Candida antarctica. This two step lipase-catalyzed process for the resolution of a chiral arylalkylamine involves a high-conversion enantioselective condensation of (R)-(+)-1-phenylethylamine with capric acid (conversion 99%, <24 h), followed by the hydrolysis of the corresponding synthesized (R)-(+)-amide (conversion 98%, 48 h). As a result, this efficient enzymatic process yields both (R)- and (S)-enantiomers of 1-phenylethylamine in high enantiomeric purity.

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N-[(R)-(+)-1-Phenylethyl]decanamideC18H29NOYield 95%, ee > 99%[α]D24=+67.5 (c 0.7, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (R)

(S)-(−)-1-PenylethylamineC8H11NYield 90%, calcd ee > 97%[α]D24=-30.6 (c 9.6, EtOH)Source of chirality: enzymatic resolutionAbsolute configuration: (R)

(R)-(+)-1-PhenylethylamineC8H11NYield 98%, ee > 99%[α]D24=+29.8 (c 9.6, EtOH)Source of chirality: enzymatic resolutionAbsolute configuration: (R)