(S)-Methyl pyrrolidine-3-carboxylate

Base Information

• Chemical Name: (S)-Methyl pyrrolidine-3-carboxylate
• CAS No.: 216311-60-3
• Molecular Formula: C6H11 N O2
• Molecular Weight: 129.159
• DSSTox Substance ID: DTXSID70363770
• Nikkaji Number: J1.020.579D
• Wikidata: Q72497139
• Mol file: 216311-60-3.mol

Synonyms:(S)-METHYL PYRROLIDINE-3-CARBOXYLATE;216311-60-3;methyl (3S)-pyrrolidine-3-carboxylate;3-PYRROLIDINECARBOXYLIC ACID, METHYL ESTER, (3S)-;SCHEMBL12699753;DTXSID70363770;methyl (S)-pyrrolidine-3-carboxylate;AKOS006239586;BS-24984;(S)-METHYLPYRROLIDINE-3-CARBOXYLATE;S-3-Pyrrolidinecarboxylic acid methyl ester;CS-0053780;A26480;EN300-1069196;(3S)-Pyrrolidine-3beta-carboxylic acid methyl ester

Chemical Property of (S)-Methyl pyrrolidine-3-carboxylate

Chemical Property:

• Boiling Point: 170℃
• PKA: 9.42±0.10(Predicted)
• Flash Point: 57℃
• PSA: 38.33000
• Density: 1.055
• LogP: 0.09770
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

NLT 98% ^*data from raw suppliers

(S)-methylpyrrolidine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCNC1
• Isomeric SMILES: COC(=O)[C@H]1CCNC1

Technology Process of (S)-Methyl pyrrolidine-3-carboxylate

There total 8 articles about (S)-Methyl pyrrolidine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

methyl (S)-(+)-1-(phenylmethyl)-3-pyrrolidinecarboxylate (216311-58-9) → (3S)-pyrrolidine-3-carboxylic acid methyl ester (216311-60-3,72057-18-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 16h; under 759.8 Torr; Ambient temperature;

DOI:10.1055/s-1998-2185

Reference yield:

(S)-1-benzylpyrrolidine-3-carbonitrile (159063-16-8) → (3S)-pyrrolidine-3-carboxylic acid methyl ester (216311-60-3,72057-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HCl, H₂O / 0.5 h / Heating

2: SOCl₂ / 1.) -50 deg C to room temp., 3 h, 2.) room temp., 11 h

3: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol / 16 h / 759.8 Torr / Ambient temperature

With hydrogenchloride; thionyl chloride; water; hydrogen; palladium dihydroxide; In methanol;

DOI:10.1055/s-1998-2185

Reference yield:

Methanesulfonate(R)-1,1-dibenzyl-3-methanesulfonyloxy-pyrrolidinium; → (3S)-pyrrolidine-3-carboxylic acid methyl ester (216311-60-3,72057-18-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 20percent Pd(OH)2/C / ethanol / 0.33 h / 757.6 Torr

2: 93 percent / Bu₄NCN / dimethylsulfoxide / 60 h / 60 - 65 °C

3: HCl, H₂O / 0.5 h / Heating

4: SOCl₂ / 1.) -50 deg C to room temp., 3 h, 2.) room temp., 11 h

5: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol / 16 h / 759.8 Torr / Ambient temperature

With hydrogenchloride; thionyl chloride; water; hydrogen; tetra-n-butylammonium cyanide; palladium dihydroxide; In methanol; ethanol; dimethyl sulfoxide;

DOI:10.1055/s-1998-2185

upstream raw materials:

methyl (S)-(+)-1-(phenylmethyl)-3-pyrrolidinecarboxylate

methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate

Dimethyl itakonate

(S)-(+)-1-(phenylmethyl)-5-oxo-3-pyrrolidinecarboxylic acid

Downstream raw materials:

(S)-1-(4’-(4-(trifluoromethyl)cyclohexyloxy)biphenylcarbonyl)pyrrolidine-3-carboxylic acid

C₃₀H₃₆ClFN₂O₅

C₂₈H₃₂ClFN₂O₅

C₂₈H₃₂ClFN₂O₆

Refernces

• 1、 Thomas,Ohnmacht,Zahn,Mohr,Gmeiner, Peter. "Ex-chiral pool synthesis and pharmacological aspects of 3- pyrrolidinylisoxazoles". . p. 248 - 250. Retrieved 2007/10/03.