| Identification | Back Directory | [Name]
(3S,4S)-Pyrrolidine-3,4-diol | [CAS]
90481-32-6 | [Synonyms]
EOS-62153
(3S,4S)-3,4-Pyrrolidinediol
(3s,4s)-pyrrolidine-3,4-dio
(3S,4S)-Pyrrolidine-3,4-diol
1,4-dideoxy-1,4-iminothreitol
3,4-Pyrrolidinediol, (3S,4S)-
(3S,4S)-3,4-Dihydroxypyrrolidine | [Molecular Formula]
C4H9NO2 | [MDL Number]
MFCD08686737 | [MOL File]
90481-32-6.mol | [Molecular Weight]
103.12 |
| Chemical Properties | Back Directory | [Boiling point ]
232 °C | [density ]
1.309 | [Fp ]
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 Rotation]
20.6°(C=1.10g/100ml MEOH) |
| Hazard Information | Back Directory | [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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