| Identification | Back Directory | [Name]
PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER | [CAS]
145681-01-2 | [Synonyms]
t-BOC-L-Pro-OMe
Boc-DL-proline Methyl ester
Methyl 1-Boc-2-pyrrolidinecarboxylate
Methyl N-Boc-Pyrrolidine-2-Carboxylate
1-Boc-2-pyrrolidinecarboxylic acid Methyl ester
1-O-tert-butyl 2-O-methyl pyrrolidine-1,2-dicarboxylate
1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-diMethylethyl) 2-Methyl ester | [Molecular Formula]
C11H19NO4 | [MDL Number]
MFCD03762834 | [MOL File]
145681-01-2.mol | [Molecular Weight]
229.27 |
| Chemical Properties | Back Directory | [Boiling point ]
288.6±33.0 °C(Predicted) | [density ]
1.120±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
-3.35±0.40(Predicted) | [Appearance]
Colorless to light yellow Liquid |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of methyl 1-Boc-2-pyrrolidinecarboxylate from Boc-L-proline and iodomethane was as follows: potassium carbonate (K2CO3, 1.1 kg, 8.0 mol) and iodomethane (CH3I, 659 g, 4.65 mol) were added to a 1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (500 g, 2.32 mol) in a solution of dimethylformamide (DMF, 2.5 L). The reaction mixture was stirred at room temperature for 12 h followed by filtration. The filtrate was concentrated under vacuum. The residue was dissolved in ethyl acetate (EtOAc, 2 L), washed sequentially with water (2 x 1 L) and brine (1 L), dried with magnesium sulfate (MgSO4), and finally concentrated under vacuum to afford methyl 1-Boc-2-pyrrolidinecarboxylate (417.8 g, 96% yield) as a yellow oil.1H NMR (CDCl3) data were as follows: δ 1.37 (9H m), 1.72-1.84 (3H, m), 2.15 (1H, m), 3.26-3.51 (2H, m), 3.65 (3H, s), 4.17 (1H, m). | [References]
[1] Patent: WO2013/14448, 2013, A1. Location in patent: Page/Page column 103
[2] Patent: WO2016/89977, 2016, A1. Location in patent: Paragraph 00137
[3] Patent: WO2014/28675, 2014, A1. Location in patent: Page/Page column 118
[4] Patent: WO2016/138532, 2016, A1. Location in patent: Paragraph 0376
[5] Tetrahedron Asymmetry, 2003, vol. 14, # 10, p. 1323 - 1333 |
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