(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid Property

storage temp. 

2-8°C

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..…

(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid Chemical Properties,Usage,Production

Uses

(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid is a cyclic amino acid derivative that is used in the synthesis of peptides and peptidomimetics. It contains a pyrrolidine ring and a carboxylic acid group at position 2. This compound is an optical isomer, and its (S)-stereoisomer is the most commonly used in scientific experiments, such as synthesizing tert-butyl (S)-2-(hydroxymethyl)-4,4-dimethylpyrrolidine-1-carboxylate, (S)-4,4-dimethylpyrrolidine-2-carboxylic acid, and so on.

Synthesis

To a solution of 1-(tert-butyl) 2-methyl (S)-4,4-dimethylpyrrolidine-1,2-dicarboxylate (4.85 g, 18.86 mmol) in THF (40 mL) was dropwise added lithium hydroxide monohydrate aqueous solution (1.5 g, 20 mL)  at 0 °C. At the end of the addition, the mixture was stirred at rt for 2.0 h. After that, the THF solvent was removed and 50 mL of water was added to the mixture. The resulting mixture was washed with EtOAc (30 mL x 3). The aqueous phase was adjusted to pH=1 with hydrochloric acid (1 M) and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated in vacuo to give (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid as a white solid (4.35 g, 95%).