Methyl (S)-4,4-difluoropyrrolidine-2-carboxylate hydrochloride

Methyl (S)-4,4-difluoropyrrolidine-2-carboxylate hydrochloride Property

storage temp. 

Inert atmosphere,Room Temperature

Appearance

White to off-white Solid

optical activity

-10.9° (C=0.01 g/ml, H2O)

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

Methyl (S)-4,4-difluoropyrrolidine-2-carboxylate hydrochloride Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of (S)-4,4-difluoropyrrolidine-2-carboxylic acid methyl ester hydrochloride from N-BOC-4,4-difluoro-L-proline methyl ester: N-BOC-4,4-difluoro-L-proline methyl ester (3 g, 11.3 mmol) was mixed with EtOAc solution (15 mL) of 4 M HCl and the reaction was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was concentrated in vacuum to afford methyl (S)-4,4-difluoropyrrolidine-2-carboxylate hydrochloride (2.27 g, 100% yield) as a white solid. The structure of the compound was confirmed by the following spectral data: MS-ESI: m/z 166.14 [M + H]+; 1H NMR (400 MHz, CDCl3): δ 4.70-4.69 (m, 1H), 3.75-3.87 (m, 2H), 3.71 (s, 3H), 2.91-3.00 (m, 1H), 2.70-2.81 (m, 1H).

References

[1] Patent: EP2730572, 2015, B1. Location in patent: Paragraph 0416; 0421