| Identification | More | [Name]
(3S,4S)-1-Benzylpyrrolidine-3,4-diol | [CAS]
90365-74-5 | [Synonyms]
(3S,4S)-(+)-1-BENZYL-3,4-PYRROLIDINDIOL
(3S,4S)-(+)-1-BENZYL-3,4-PYRROLIDINEDIOL
(3S,4S)-1-BENZYL-PYRROLIDINE-3,4-DIOL
(3S
(3S,4S)-(+)-1-Benzyl-3,4-pyrrolidindiol, GC 97% | [Molecular Formula]
C11H15NO2 | [MDL Number]
MFCD01073893 | [Molecular Weight]
193.24 | [MOL File]
90365-74-5.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light brown powder or needles | [Melting point ]
94-100 °C
| [alpha ]
33.6 º (c=1.05% in methanol) | [Boiling point ]
329.46°C (rough estimate) | [density ]
1.0945 (rough estimate) | [refractive index ]
1.5041 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder, Crystals, and/or Chunks | [pka]
13.99±0.40(Predicted) | [color ]
Off-white to yellow to light brown | [Optical Rotation]
[α]20/D +33.6±3°, c = 1.05% in methanol | [BRN ]
4992458 | [InChI]
InChI=1S/C11H15NO2/c13-10-7-12(8-11(10)14)6-9-4-2-1-3-5-9/h1-5,10-11,13-14H,6-8H2/t10-,11-/m0/s1 | [InChIKey]
QJRIUWQPJVPYSO-QWRGUYRKSA-N | [SMILES]
N1(CC2=CC=CC=C2)C[C@H](O)[C@@H](O)C1 | [CAS DataBase Reference]
90365-74-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
10-34 | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light brown powder or needles | [Uses]
(3S,4S)-(+)-1-Benzyl-3,4-pyrrolidinediol can be used:
- As a building block for the preparation of novel chiral crown ethers.
- As an intermediate in the synthesis of (3R,4R)1-benzyl-4-fluoropyrrolidin-3- amine.
- As an intermediate in the preparation of 3-hydroxy-4-pyrrolidinyl analogs of nucleobases.
| [Synthesis]
Tetrahydrofuran (3.6 L) was cooled under nitrogen protection and LiAlH4 (61.2 g, 1.6 mol) was slowly added. Subsequently, a tetrahydrofuran solution of (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione (132.7 g, 0.6 mol) was added dropwise to this suspension. The reaction mixture was refluxed for 12 h and cooled to room temperature. In an ice-water bath, ethyl acetate (144 mL), distilled water (61.2 mL), 5% aqueous NaOH solution (61.2 mL), and distilled water (183.6 mL) were added sequentially and slowly dropwise while maintaining vigorous stirring. The reaction mixture was filtered and the filter cake was washed with hot tetrahydrofuran (2 x 1.2 L). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give a light yellow oil. The oil was recrystallized from ethyl acetate to give (3S,4S)-1-benzylpyrrolidine-3,4-diol (82.3 g, 71.0% yield) as a white solid. | [References]
[1] Tetrahedron, 2007, vol. 63, # 5, p. 1243 - 1253
[2] Angewandte Chemie, 1984, vol. 96, # 6, p. 425 - 426
[3] Patent: CN105693520, 2016, A. Location in patent: Paragraph 0148; 0149; 0159; 0151; 0152; 0153
[4] Patent: EP3067351, 2016, A1. Location in patent: Paragraph 0071; 0072
[5] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2219 - 2224 |
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