N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol Chemical Properties

Melting point:

60-64 °C (lit.)

alpha 

26 º (c=1%, MeOH)

Boiling point:

273.3±33.0 °C(Predicted)

Density 

1.142±0.06 g/cm3(Predicted)

refractive index 

27 ° (C=1, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

14.74±0.20(Predicted)

form 

Crystalline Powder

color 

White to pale yellow

optical activity

[α]20/D +26°, c = 1% in methanol

BRN 

6271108

InChI

InChI=1S/C9H17NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h7,11H,4-6H2,1-3H3/t7-/m0/s1

InChIKey

APCBTRDHCDOPNY-ZETCQYMHSA-N

SMILES

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

CAS DataBase Reference

101469-92-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25-37/38-41-R41-R37/38-R25

Safety Statements 

26-39-45-S45-S39-S26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

F 

10

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(S)-(+)-N-Boc-3-pyrrolidinol can be used as a reactant to synthesize:

• tert-Butyl 3-(2-bromophenoxy)pyrrolidine-1-carboxylate, which is employed as a key intermediate in the preparation of IkB-kinase IKK2 inhibitor.
• Dimethoxy-pyrrolidylquinazoline , and peptidomimetic quinoline derivatives.

Synthesis

The general procedure for the synthesis of 1-tert-butoxycarbonyl-3-hydroxy-pyrrolidine from di-tert-butyl dicarbonate and 3-hydroxy-pyrrolidine was as follows: first, (R)-3-pyrrolidinol (539 mg, 6.19 mmol) was converted into compound 16b to afford a colorless oily substance (1.3 g, 100% yield). The spectral data of this product 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 16e was prepared from compound 16c by a two-step reaction, still as a colorless oily substance. Finally, compound 16e was further reacted to obtain the target product 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

N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol(101469-92-5)Related Product Information

• N-Boc-cis-4-Hydroxy-L-proline
• (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid
• N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol
• (3R,4R)-tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate
• N-Boc-cis-4-Hydroxy-L-proline methyl ester
• (R)-1-Boc-3-hydroxypyrrolidine
• 1-(tert-Butoxycarbonyl)-3-pyrrolidinol
• 3-Pyrrolidinol
• DL-3-PYRROLIDINOL
• (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID
• BOC-4-HYDROXY-L-PYRROLIDINE LACTONE
• BOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
• BOC-CIS-3-HYDROXY-D-PROLINE
• (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-PHENOXY-2-PYRROLIDINECARBOXYLIC ACID
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• BOC-CISHYP(BZL)-OH
• (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-CHLORO-4-FLUOROPHENOXY)-2-PYRROLIDINECARBOXYLIC ACID
• (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(4-CHLORO-2-FLUOROPHENOXY)-2-PYRROLIDINECARBOXYLIC ACID