Expeditious novel routes to enantiopure 3-amino tetrahydrofuran hydrochloride

The synthesis of chemically and enantiomerically pure (S)-3-amino tetrahydrofuran hydrochloride starting from the natural amino acids, l-aspartic acid or l-methionine is described. The process involves no chromatography and can be easily carried out on a large scale. The enantiopurity of the final product was established by NMR and chiral HPLC methods.

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(S)-3-Aminotetrahydrofuran hydrochlorideC4H10ClNOee ⩾99%[α]D27 = −10.2 (c 1.0, methanol)Source of chirality: l-aspartic acid/l-methionineAbsolute configuration: (S)

(S)-2-Benzoylamino gamma butyrolactoneC11H11NO3ee ⩾99%[α]D27 = −27.8 (c 1.0, ethanol)Source of chirality: l-methionineAbsolute configuration: (S)

(S)-3-Benzoylamino tetrahydrofuranC11H13NO2ee ⩾99%[α]D27 = −29.4 (c 1.0, methanol)Source of chirality: l-aspartic acid/l-methionineAbsolute configuration: (S)

(S)-2-Benzoylaminobutane 1,4 diolC11H15NO3ee ⩾99%[α]D27 = −39.7 (c 0.05, methanol)Source of chirality: l-aspartic acid/l-methionineAbsolute configuration: (S)