Methyl pyrrolidine-2-carboxylate hydrochloride Chemical Properties

Melting point:

69-71°C

refractive index 

32 ° (C=1, H2O)

storage temp. 

2-8°C

solubility 

Methanol (Slightly), Water (Slightly, Sonicated)

form 

Powder or Crystalline Powder

color 

White

optical activity

[α]/D 33.0±2.0°, c = 1 in H2O

Sensitive 

Hygroscopic

BRN 

4714125

CAS DataBase Reference

65365-28-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38-36/37/38

Safety Statements 

26-36-28

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

Methyl pyrrolidine-2-carboxylate hydrochloride Usage And Synthesis

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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