(R)-1-Boc-3-cyanopyrrolidine

(R)-1-Boc-3-cyanopyrrolidine Property

Boiling point:

307.9±35.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

-3.73±0.40(Predicted)

Appearance

white solid

optical activity

[α]/D -21.0±2.0°, c = 1 in methanol

BRN 

8683216

CAS DataBase Reference

132945-76-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(R)-1-Boc-3-cyanopyrrolidine Chemical Properties,Usage,Production

Uses

(R)-1-Boc-3-cyanopyrrolidine can be used as a key intermediate in the synthesis of a β-proline analog named (3R)-carboxy pyrrolidine.

Uses

(R)-1-Boc-3-cyanopyrrolidine is used in the preparation of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid compounds as anti-microbial agents.

Synthesis

The general procedure for the synthesis of (R)-1-Boc-3-cyanopyrrolidine from the compound (CAS: 773837-37-9) and S-1-Boc-3-OMS-pyrrolidine is as follows: b) Synthesis of 1,1-dimethylethyl (3R)-3-cyano-1-pyrrolidine carboxylate A mixture of 1,1-dimethylethyl (3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidine carboxylic acid ester (211 mmol) with sodium cyanide (633 mmol) in N,N-dimethylformamide (300 mL) was stirred vigorously for 18 h at 100 °C in a nitrogen atmosphere using a mechanical stirrer. After completion of the reaction, the mixture was cooled to room temperature, filtered and washed well with ether. The filtrate was diluted with dilute brine and extracted with ether (4 x 700 mL). The organic extracts were combined, washed with dilute brine, filtered through a pad of sodium sulfate and subsequently concentrated under vacuum. The residue was purified by fast chromatography (eluent: 0-50% ethyl acetate/hexane) to afford the target product (141 mmol, 67% yield). 1H NMR (400 MHz, CDCl3) δ ppm: 1.48 (s, 9H), 2.14-2.37 (m, 2H), 3.00-3.20 (m, 1H), 3.45 (dt, J = 11.05, 6.98 Hz, 1H), 3.53-3.66 (m, 2H), 3.65-3.76 (m, 1H).

References

[1] Patent: WO2011/56635, 2011, A1. Location in patent: Page/Page column 49-50
[2] Patent: WO2011/66211, 2011, A1. Location in patent: Page/Page column 35
[3] Patent: WO2013/28445, 2013, A1. Location in patent: Page/Page column 51
[4] Patent: WO2012/37298, 2012, A1. Location in patent: Page/Page column 82