(3S,4S)-1-Benzylpyrrolidine-3,4-diol Chemical Properties

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)

pka

13.99±0.40(Predicted)

form 

Powder, Crystals, and/or Chunks

color 

Off-white to yellow to light brown

optical activity

[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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

F 

10-34

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(3S,4S)-1-Benzylpyrrolidine-3,4-diol Usage And Synthesis

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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