BOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

157℃

Boiling point:

390.9±42.0 °C(Predicted)

Density 

1.312±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

2-8°C

pka

3.69±0.40(Predicted)

Appearance

White to light brown Solid

Safety Information

HazardClass 

IRRITANT

BOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of N-Boc-(2S,3S)-(2S,3S)-3-hydroxy-2-carboxypyrrolidine from (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester: to 1-(tert-butoxycarbonyl)-2-methyl-(2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate (0.30 g, 1.22 mmol) in a tetrahydrofuran (12 mL) solution was added to 0.2N aqueous lithium hydroxide (6.12 mL, 1.22 mmol). The reaction mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction mixture was diluted with ether (30 mL) and extracted with 0.2N aqueous lithium hydroxide solution (3 x 5 mL). The aqueous layers were combined and acidified with 5% aqueous hydrochloric acid to pH=2. The acidic aqueous layer was extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to afford N-Boc-(2S,3S)-3-hydroxy-2-carboxypyrrolidine as a gel (0.25 g, 88% yield), which was used directly in the next reaction. Mass spectrum (ES+) m/z 230.3 (M+1).

References

[1] Patent: WO2016/7534, 2016, A1. Location in patent: Page/Page column 171; 172

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