(3S,4S)-Pyrrolidine-3,4-diol Chemical Properties

Boiling point:

232 °C

Density 

1.309

Flash point:

144 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

14.08±0.40(Predicted)

Appearance

White to off-white Solid

optical activity

20.6°(C=1.10g/100ml MEOH)

(3S,4S)-Pyrrolidine-3,4-diol Usage And Synthesis

Synthesis

General procedure for the synthesis of (3S,4S)-pyrrolidine-3,4-diol from (3S,4S)-1-benzylpyrrolidine-3,4-diol: 10% palladium-carbon catalyst (100 mg) and acetic acid (10 mL) were added to a solution of (3S,4S)-1-benzylpyrrolidine-3,4-diol (522 mg) in ethanol (15 mL). The mixture was placed in a Parr hydrogenation unit and reacted at 40 psi hydrogen pressure for 7 hours at room temperature. Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. To the concentrated residue was added 4N hydrochloric acid-dioxane solution and concentrated again under reduced pressure to give (3S,4S)-pyrrolidine-3,4-diol (373 mg) as a yellow solid in 99% yield. Mass spectrum (APCI) m/z: 104 [M + H]+.

References

[1] Synthetic Communications, 2008, vol. 38, # 14, p. 2374 - 2384
[2] Patent: EP2390254, 2011, A1. Location in patent: Page/Page column 86
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 16, p. 2385 - 2390
[4] Angewandte Chemie, 1984, vol. 96, # 6, p. 425 - 426
[5] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 3965 - 3973

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