(R)-2-Methylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (R)-2-Methylpyrrolidine-2-carboxylic acid
• CAS No.: 63399-77-9
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2933990090
• European Community (EC) Number: 817-966-1
• DSSTox Substance ID: DTXSID60979566
• Nikkaji Number: J774.186C
• Mol file: 63399-77-9.mol

Synonyms:63399-77-9;(R)-2-Methylpyrrolidine-2-carboxylic acid;(R)-2-Methylproline;H-ALPHA-ME-D-PRO-OH;(2R)-2-methylpyrrolidine-2-carboxylic acid;2-methyl-D-proline;MFCD08274534;d-alpha-methylproline;alpha-Me-D-Pro-OH;alpha-Methyl-D-proline;SCHEMBL3325667;AMY4324;DTXSID60979566;LWHHAVWYGIBIEU-ZCFIWIBFSA-N;BCP01614;CS-M0572;AKOS006286736;DS-4792;(R)-2-Methylpyrrolidine-2-carboxylicacid;AC-31037;(R)-2-Methyl-2-pyrrolidinecarboxylic acid;(R)-2-Methyl-pyrrolidine-2-carboxylic acid;EN300-267079;F14122

Chemical Property of (R)-2-Methylpyrrolidine-2-carboxylic acid

Chemical Property:

• Melting Point: 340 °C
• Boiling Point: 241.912 °C at 760 mmHg
• PKA: 2.44±0.20(Predicted)
• Flash Point: 100.105 °C
• PSA: 49.33000
• Density: 1.119 g/cm³
• LogP: 0.54190
• Storage Temp.: Store at 0°C
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 135

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-2-MethylProline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCN1)C(=O)O
• Isomeric SMILES: C[C@@]1(CCCN1)C(=O)O
• Uses: (R)-2-Methyl Proline is a derivative of D-Proline (P755990) which is used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.

Technology Process of (R)-2-Methylpyrrolidine-2-carboxylic acid

There total 10 articles about (R)-2-Methylpyrrolidine-2-carboxylic acid 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: 90.0%

DL-(α-methyl)proline amide (848488-83-5) → (S)-2-methylpyrrolidine-2-carboxylic acid (42856-71-3) + (R)-2-Methyl-1-azacyclopentan-2-carbonsaeure (63399-77-9)

Guidance literature:

With hydrogenchloride; water; at 90 ℃; for 4h;

Reference yield: 51.0%

DL-(α-methyl)proline amide (848488-83-5) → (S)-2-methylpyrrolidine-2-carboxylic acid amide (132235-43-9) + (2R)-2-methyl-2-pyrrolidinecarboxamide (132235-42-8) + (R)-2-Methyl-1-azacyclopentan-2-carbonsaeure (63399-77-9)

Guidance literature:

With Mycobacterium neoaurum ATCC 25795 amidase; acetic acid; In water; at 37 ℃; for 70h; pH=8.5; optical yield given as %ee; stereoselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/chem.200900688

Reference yield:

5-chloro-2-pentanone (5891-21-4) → (S)-2-methylpyrrolidine-2-carboxylic acid (42856-71-3) + (R)-2-Methyl-1-azacyclopentan-2-carbonsaeure (63399-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonium acetate / water; tert-butyl alcohol / 2.5 h / 50 °C

1.2: 2.5 h

1.3: 24 h / 15 - 20 °C

2.1: hydrogenchloride; water / 4 h / 90 °C

With hydrogenchloride; ammonium acetate; water; In water; tert-butyl alcohol;

upstream raw materials:

(S)-3-Isopropyl-1-methoxy-8a-methyl-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-4-one

DL-(α-methyl)proline amide

5-chloro-2-pentanone

1-benzyl-2-methylpyrrolidine-2-carbonitrile

Downstream raw materials:

(R)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid

tert-butyl (R)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

veliparib

(7aR)-7a-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3]oxazole-1,3-dione

Refernces

• 1、 -. "METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE". . . Retrieved 2014/05/06.
• 2、 Schoellkopf, Ulrich,Hinrichs, Rolf,Lonsky, Ralph. "Asymmetrische Synthese cyclischer α-Aminosaeuren nach der Bislactimether-Methode". . p. 137 - 138. Retrieved 2007/10/02.