(3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL Chemical Properties

Melting point:

94-100 °C

Boiling point:

329.46°C (rough estimate)

Density 

1.0945 (rough estimate)

refractive index 

1.5041 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

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 

6478637

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-/m1/s1

InChIKey

QJRIUWQPJVPYSO-GHMZBOCLSA-N

SMILES

N1(CC2=CC=CC=C2)C[C@@H](O)[C@H](O)C1

CAS DataBase Reference

163439-82-5

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

10-34

HS Code 

29339900

MSDS

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

(3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL Usage And Synthesis

Chemical Properties

off-white to light brown powder

Synthesis

General procedure for the synthesis of (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione from (3R,4R)-1-benzyl-3,4-pyrrolidinediol: a tetrahydrofuran solution of borane (1.0 M, 17.19 mL, 180.99 mmol) was added slowly and dropwise to a tetrahydrofuran solution (1.0 M, 17.19 mL, 180.99 mmol) of (3R,4R)-1-benzyl-3,4-dihydroxy pyrrolidine-2,5-dione (10.0 g, 45.24 mmol) in a solution of tetrahydrofuran (200 mL). After dropwise addition, the reaction mixture was slowly heated to 70°C and kept at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 0°C and the reaction was quenched by the dropwise addition of methanol (50 mL), noting that a strong gas release occurs at this point. Subsequently, the mixture was slowly warmed to room temperature and stirring was continued for 1 hour. The reaction mixture was concentrated under vacuum and the crude product was purified by silica gel column chromatography using a linear gradient elution of ethyl acetate in petroleum ether to afford 7.73 g (88.5% yield) of the yellow crystalline product (3R,4R)-1-benzyl-3,4-pyrrolidinediol. Specific optical rotation (MeOH, 0.5%): +22.800°; 1H NMR (400 MHz, DMSO-d6) δ 7.51-7.49 (2H, m), 7.39-7.37 (3H, m), 5.45 (1H, d, J = 4.4 Hz, OH), 5.20 (1H, d, J = 5.2 Hz, OH), 4.15- 4.11 (1H, m), 4.04-3.94 (2H, m), 3.90-3.85 (1H, m), 3.48-3.43 (1H, m), 3.10-3.06 (1H, m), 2.97-2.93 (1H, m), 2.89-2.86 (1H, m); 13C NMR (100 MHz, DMSO-d6) δ 132.86, 128.97, 128.51, 127.73, 76.27, 65.47, 63.24; LC-MS (ESI) m/z Calculated value C11H15NO2 [M + H]+: 193.11, measured value: 194.20.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2818 - 2823
[2] Synlett, 2009, # 12, p. 1945 - 1948

(3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL(163439-82-5)Related Product Information

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