A facile enantioselective synthesis of enantiomerically pure (R)-phenoxybenzamine hydrochloride using the hydrolytic kinetic resolution method

A practical and highly efficient enantioselective synthesis of (R)-phenoxybenzamine hydrochloride has been described for the first time using Jacobsen’s hydrolytic kinetic resolution of a terminal epoxide as a key step and source of chirality.

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(S)-1-Phenoxypropan-2-olC9H12O2[α]D25=+36.6 (c 1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (S)

(R)-N-Benzyl-2-nitro-N-(1-phenoxypropan-2-yl)benzenesulfonamideC22H22N2O5S[α]D25=+45.4 (c 1, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)

(R)-N-Benzyl-1-phenoxypropan-2-amineC16H19NO[α]D25=+10.7 (c 4, EtOH)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)

(R)-2-Benzyl-N-(2-hydroxyethyl)-1-phenoxyisopropylamineC18H23NO2[α]D25=+15.4 (c 4.1, EtOH)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)

(R)-N-Benzyl-N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-amine·HClC18H23Cl2NO[α]D25=+17.6 (c 4, EtOH)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R)