(2S,4R)-4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester Chemical Properties

Melting point:

75-78 °C

Boiling point:

282.5±33.0 °C(Predicted)

Density 

1.094±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.75±0.40(Predicted)

Appearance

White to yellow Solid

optical activity

20.6°(C=0.01g/100mL, DCM, 20°C, 589nm)

InChI

InChI=1S/C10H19NO3/c1-7-5-8(12)6-11(7)9(13)14-10(2,3)4/h7-8,12H,5-6H2,1-4H3/t7-,8+/m0/s1

InChIKey

BXZADLGAYWRZCR-JGVFFNPUSA-N

SMILES

N1(C(OC(C)(C)C)=O)C[C@H](O)C[C@@H]1C

(2S,4R)-4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester Usage And Synthesis

Synthesis

Tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-methylpyrrolidine-1-carboxylate (2.2 g, 6.98 mmol) was dissolved in tetrahydrofuran (30 mL), followed by addition of tetrabutylammonium fluoride (3.65 g, 14.0 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was poured into water (60 mL) and extracted with ethyl acetate (60 mL x 2). The organic phases were combined, washed with saturated sodium chloride solution (60 mL x 2) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by column chromatography (petroleum ether: ethyl acetate = 2:1) to give 1.47 g of a yellow oily product, i.e. tert-butyl (2S,4R)-4-hydroxy-2-methylpyrrolidine-1-carboxylate in 99% yield.

References

[1] Patent: EP3401315, 2018, A1. Location in patent: Paragraph 0106; 0111
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 8, p. 1598 - 1611
[3] Journal of the American Chemical Society, 2008, vol. 130, # 3, p. 875 - 886

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