| Identification | More | [Name]
Methyl pyrrolidine-2-carboxylate hydrochloride | [CAS]
65365-28-8 | [Synonyms]
D-PROLINE METHYL ESTER HCL
D-PROLINE METHYL ESTER HYDROCHLORIDE
D-PROLINE METHYL ESTER HYDROCHLORIDE SALT
D-PROLINE-OME HCL
D-PYRROLIDINE-2-CARBOXYLIC ACID-METHYL ESTER HCL
H-D-PRO-OME HCL
METHYL D-PROLINATE HYDROCHLORIDE
D-proline methy ester hydrochloride
D-Pro-Ome.Hcl
Methyl pyrrolidine-2-carboxylate hydrochloride
Pyrrolidine-2-carboxylic acid methyl ester hydrochloride | [EINECS(EC#)]
-0 | [Molecular Formula]
C6H12ClNO2 | [MDL Number]
MFCD00083685 | [Molecular Weight]
165.62 | [MOL File]
65365-28-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
69-71°C | [refractive index ]
32 ° (C=1, H2O) | [storage temp. ]
-15°C | [solubility ]
Methanol (Slightly), Water (Slightly, Sonicated) | [form ]
Powder or Crystalline Powder | [color ]
White | [Optical Rotation]
[α]/D 33.0±2.0°, c = 1 in H2O | [Sensitive ]
Hygroscopic | [BRN ]
4714125 | [Major Application]
peptide synthesis | [InChI]
1S/C6H11NO2.ClH/c1-9-6(8)5-3-2-4-7-5;/h5,7H,2-4H2,1H3;1H/t5-;/m1./s1 | [InChIKey]
HQEIPVHJHZTMDP-NUBCRITNSA-N | [SMILES]
Cl.COC(=O)[C@H]1CCCN1 | [CAS DataBase Reference]
65365-28-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline | [Uses]
D-Proline Methyl Ester is a methyl ester 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. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general steps for the synthesis of L-proline methyl ester hydrochloride from methanol and DL-proline are as follows:
Step 1: Synthesis of methylpyrrolidine-2-carboxylic acid hydrochloride
Thionyl chloride (15.7 mL, 217.4 mmol) was slowly added dropwise to a mixed solution of DL-proline (5.0 g, 43.47 mmol) and methanol (50 mL) at about 0 °C, and the dropwise process lasted for about 15 minutes. The reaction mixture was stirred at room temperature for about 16 hours before the solvent was removed by vacuum concentration. The resulting gel was ground with n-pentane, decanted and dried to give D-proline methyl ester hydrochloride as an off-white solid (6.25 g, 87% yield).
The product characterization data were as follows:
1H NMR (400 MHz, DMSO-d6) δ 1.87-2.04 (m, 3H), 2.21-2.28 (m, 1H), 3.22-3.26 (m, 2H), 3.75 (s, 3H), 4.34 (t, J = 7.8 Hz, 1H).
IR (film) υ 3513, 3130, 2597, 1740, 1632, 1452, 1402, 1245, 1178, 1046, 764 cm-1;
MS 130 (M + 1). | [References]
[1] Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 584 - 596
[2] Patent: US2010/105755, 2010, A1. Location in patent: Page/Page column 11-12
[3] Molecules, 2008, vol. 13, # 5, p. 1111 - 1119
[4] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2775 - 2781
[5] Patent: US2008/76758, 2008, A1. Location in patent: Page/Page column 91; 93 |
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