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

(3S,4S)-Pyrrolidine-3,4-diol Property

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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

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