1-(tert-Butoxycarbonyl)-3-pyrrolidinol Chemical Properties

Melting point:

62.1-62.2°C

Boiling point:

273.3±33.0 °C(Predicted)

Density 

1.142±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

14.74±0.20(Predicted)

color 

White to Almost white

optical activity

Consistent with structure

InChI

InChI=1S/C9H17NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h7,11H,4-6H2,1-3H3

InChIKey

APCBTRDHCDOPNY-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(O)C1

CAS DataBase Reference

103057-44-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-25

Safety Statements 

26-36/37/39-37-45-36/37

RIDADR 

2811

WGK Germany 

2

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29339900

1-(tert-Butoxycarbonyl)-3-pyrrolidinol Usage And Synthesis

Chemical Properties

White Solid

Uses

1-Boc-3-pyrrolidinol is an intermediate for the preparation of pyrrolidinone-containing pseudopeptides, inhibitors of HIV-1 protease.

Synthesis

The general procedure for the synthesis of 1-tert-butoxycarbonyl-3-hydroxy-pyrrolidine from di-tert-butyl dicarbonate and 3-hydroxy-pyrrolidine was carried out as follows: firstly, (R)-3-pyrrolidinol (539 mg, 6.19 mmol) was converted to compound 16b to afford the colorless oily material (1.3 g, 100% yield). The spectral data of this compound were consistent with the expected structure and in accordance with literature reports (see Kucznierz, R. et al. J. Med. Chem. 1998, 41, 4983-4994). Subsequently, compound 16b was converted by reaction to compound 16c, again as a colorless oil. Next, compound 16c was converted by a two-step reaction to compound 16e, still a colorless oily substance. Finally, compound 16e was reacted to produce the target compound 16, which was rendered as a yellow oily substance.

References

[1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 10, p. 969 - 973
[2] Patent: WO2015/9731, 2015, A2. Location in patent: Paragraph 00106
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 25, p. 4983 - 4994
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 5812 - 5832
[5] Patent: WO2010/84767, 2010, A1. Location in patent: Page/Page column 86

1-(tert-Butoxycarbonyl)-3-pyrrolidinol(103057-44-9)Related Product Information

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