Zinc04202762

Zinc04202762 - Names and Identifiers

Name	Methyl 3-pyrrolidinecarboxylate
Synonyms	Zinc04202762 Zinc04202763 METHYL-PROLINATE Methylpyrrolidin-3-carboxylat Methyl 3-pyrrolidinecarboxylate METHYL 3-PYRROLIDINECARBOXYLATE methyl pyrrolidine-3-carboxylate METHYL PYRROLIDINE-3-CARBOXYLATE methyl pyrrolidine-3-carboxylate.HCl NUR NOCH ALS AST63827 !! METHYL-PROLINATE 3-pyrrolidinecarboxylic acid, methyl ester PYRROLIDINE-3-CARBOXYLIC ACID METHYL ESTER
CAS	98548-90-4
InChI	InChI=1/C6H11NO2/c1-9-6(8)5-2-3-7-4-5/h5,7H,2-4H2,1H3

Zinc04202762 - Physico-chemical Properties

Molecular Formula	C6H11NO2
Molar Mass	129.16
Density	1.055±0.06 g/cm3(Predicted)
Boling Point	92 °C(Press: 17 Torr)
Flash Point	56.5°C
Vapor Presure	1.51mmHg at 25°C
pKa	9.42±0.10(Predicted)
Storage Condition	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Refractive Index	1.447

Zinc04202762 - Risk and Safety

Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.

Zinc04202762 - Reference Information

Application

methyl 3-pyrrolidinecarboxylate can be used as a pharmaceutical synthesis intermediate, it can be prepared from benzyl-trimethylsilylmethylamine as a reaction raw material, and it can also be prepared from methyl 1-benzyl-2-oxypyrrolidine-4-carboxylate as a reaction raw material.

preparation

Step 1: charge benzyl-trimethylsilylmethylamine (100g,517mmol,1 eq) into a 1L jacketed reactor, 400ml of THF was then loaded. The reaction temperature was set to 15 °c and a 37% aqueous solution of formaldehyde (53ml, 647mmol,1.25 eq.) was added dropwise over about 10 minutes, keeping the temperature <30 °c. Step 2: In a separate reactor, charge 400ml of THF(Tj = 25°C), then add N-methylmorpholine (2.85mL,26mmol,0.05 equiv), trifluoroacetic acid (TFA)(1mL,13mmol,0.025 EQ) and methyl acrylate (56.5mL,621mmol,1.2 EQ). The solution was heated to 50-55 °c and the solution from reactor A was added dropwise over about 50 minutes. About 30 minutes after the end of the addition (reaction was complete as judged by IPC), the reactor was cooled to room temperature and the solution was concentrated to about 500ml. 250ml heptane was added and the organic phase was washed twice with 250ml water. The organic phase was dried over MgSO4 and concentrated under reduced pressure (down to 10-20mbar,45 °c). N-Bn G of the crude product 1, 4-pyrrolidine were obtained (90% yield). Step 3: 1kg N-Bn-pyrrolidine (4414mmol,1 equiv) was dissolved in 10L of methanol and hydrogenated over 101g PD/C(95mmol PD, 0.02 equiv) at atmospheric pressure. After completion of the reaction, the catalyst was filtered and the solution was concentrated to about 10L, and 2L of methanol was added and distilled at a constant volume to give methyl 3-pyrrolidinecarboxylate.

Last Update：2024-04-09 20:49:11