(R)-1-Boc-3-hydroxypyrrolidine Chemical Properties

Melting point:

62-65 °C(lit.)

alpha 

-7 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. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

14.74±0.20(Predicted)

form 

Powder

color 

White to off-white

optical activity

[α]20/D 26±1, c = 1 in methanol

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-/m1/s1

InChIKey

APCBTRDHCDOPNY-SSDOTTSWSA-N

SMILES

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

CAS DataBase Reference

109431-87-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-53-50-50/53

Safety Statements 

26-36

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

(R)-1-Boc-3-hydroxypyrrolidine Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

Used in synthesis of ligands for the nicotinic acetylcholine receptor.

Synthesis

1-tert-butoxycarbonyl-3-hydroxy-pyrrolidine (compound 16) was synthesized by a four-step reaction using di-tert-butyl dicarbonate and 3-hydroxy-pyrrolidine. First, (R)-3-pyrrolidinol (539 mg, 6.19 mmol) was converted to compound 16b to afford a colorless oily product (1.3 g, 100% yield). The spectral data of the 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 further converted 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 converted to the target product compound 16 to give 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

(R)-1-Boc-3-hydroxypyrrolidine(109431-87-0)Related Product Information

• N-Vinyl-2-pyrrolidone
• Pyrrolidine
• tert-Butanol
• 3-Pyrrolidinol
• tert-Butyl peroxyacetate
• N-Methyl-2-pyrrolidone
• tert-Butyl acetate
• Polyvinylpyrrolidone
• Povidone iodine
• (R)-1-BOC-2-METHYL-PYRROLIDINE
• (R)-N-Boc-3-aminomethylpiperidine
• N-Boc-L-alaninol
• 1-(tert-Butoxycarbonyl)-3-pyrrolidinol
• METHYL-2-PYRROLIDONE
• (R)-3-Hydroxypyrrolidine
• DL-3-PYRROLIDINOL
• (R)-1-Boc-3-hydroxypyrrolidine
• (2S,4R)-1-(tert-butoxycarbonyl)-4-[2-chloro-5-(trifluoromethyl)phenoxy]pyrrolidine-2-carboxylic acid