1-Boc-Pyrrolidine Chemical Properties

Boiling point:

80 °C/0.2 mmHg (lit.)

Density 

0.977 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.449(lit.)

Flash point:

187 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Oil

pka

-1.28±0.20(Predicted)

color 

Clear Colorless

BRN 

4664750

InChI

InChI=1S/C9H17NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H2,1-3H3

InChIKey

LPQZERIRKRYGGM-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCC1

CAS DataBase Reference

86953-79-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

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

1-Boc-Pyrrolidine Usage And Synthesis

Chemical Properties

liquid

Uses

N-Boc-pyrrolidine may be used in the synthesis of the following:

• 2-aryl-N-boc-pyrrolidines
• scalemic 2-pyrrolidinylcuprates
• 2-alkenyl-N-Boc-pyrrolidines
• 1-deoxycastanospermine
• methylphenidate analogues
• (+)-elaeokanine A

Uses

1-Boc-pyrrolidine is a boc-protected cyclic amine used as a building block in the preparation of diastereomers by usually undergoing α'-lithiations and electrophilic substitution reactions.

General Description

N-Boc-pyrrolidine is an N-substituted pyrrolidine. It is reported that the reactivity of N-Boc-pyrrolidine towards C-H insertion reaction is 2000 times more than cyclohexane. It undergoes α-arylation in the presence of a palladium catalyst with high enantioselectivity.

Synthesis

The general procedure for the synthesis of 1-Boc-tetrandrine from tetrandrine and di-tert-butyl dicarbonate is as follows: the synthesis was carried out by a modified literature method (omitting the Sparteine chiral ligand), as specified in J. Am. Chem. Soc. 1994, 116, 3231.The steps are as follows: A) Preparation of Boc-protected pyrrolidines Triethylamine (TEA, 15.6 g, 0.15 mol) was slowly added to a dichloromethane (DCM, 150 mL) solution of pyrrolidine (10.0 g, 0.14 mol) in stirring at 0 °C. Subsequently, di-tert-butyl dicarbonate ((Boc)2O, 30.6 g, 0.14 mol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete pyrrolidine consumption. Upon completion of the reaction, the reaction mixture was washed sequentially with 1 M aqueous hydrochloric acid (100 mL) and brine, and the organic phase was dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to afford the colorless, oily product 1-Boc-tetrandrine (24.0 g, 100%), which could be used in the subsequent steps without further purification.

References

[1] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2527 - 2532
[2] Patent: WO2013/102242, 2013, A1. Location in patent: Page/Page column 94; 95
[3] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8318 - 8322
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[5] Synthesis, 2001, # 4, p. 550 - 552

1-Boc-Pyrrolidine(86953-79-9)Related Product Information

• 1-Methylpyrrolidine
• N-Vinyl-2-pyrrolidone
• Cyhalofop-butyl
• Povidone iodine
• Butyl acetate
• Buprofezin
• butyl rubber
• Butyl methacrylate
• N-Methyl-2-pyrrolidone
• Polyvinylpyrrolidone
• Pyrrole
• tert-Butyl carbazate
• tert-Butyl peroxybenzoate
• Pyrrolidine
• tert-Butanol
• 2-Butoxyethanol
• Butyl acrylate
• N-T-BOC-PYRROLE