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Greenway Gold |
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18994086298 |
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Elucigen bio Gold |
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| | N-Boc-alpha-methyl-L-proline Basic information |
| Product Name: | N-Boc-alpha-methyl-L-proline | | Synonyms: | N-BOC-A-METHYL-L-PROLINE;1-(tert-butoxycarbonyl)-2-methyl-L-proline(SALTDATA: FREE);1,2-Pyrrolidinedicarboxylic acid, 2-methyl-, 1-(1,1-dimethylethyl) ester, (2S)-;N-Boc-2-Methyl-L-proline, 97%;1-Boc-2-Methyl-L-proline;(S)-1-Boc-2-Methyl-proline;(S)-N-BOC-Α-METHYLPROLINE;N-Boc-α-methyl-L-proline | | CAS: | 103336-06-7 | | MF: | C11H19NO4 | | MW: | 229.27 | | EINECS: | | | Product Categories: | α-Methyl Amino Acids;1 | | Mol File: | 103336-06-7.mol |  |
| | N-Boc-alpha-methyl-L-proline Chemical Properties |
| Boiling point | 337.8±35.0 °C(Predicted) | | density | 1.160 | | storage temp. | 2-8°C | | pka | 4.20±0.20(Predicted) | | form | Solid | | color | White to off-white | | InChI | InChI=1S/C11H19NO4/c1-10(2,3)16-9(15)12-7-5-6-11(12,4)8(13)14/h5-7H2,1-4H3,(H,13,14)/t11-/m0/s1 | | InChIKey | YQXRKJHVAUKXRN-NSHDSACASA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC[C@@]1(C)C(O)=O |
| Hazard Codes | Xn | | Risk Statements | 22 | | HS Code | 2933998090 |
| | N-Boc-alpha-methyl-L-proline Usage And Synthesis |
| Uses | N-Boc-2-methyl-L-proline is used as pharmaceutical intermediate. | | Synthesis | (S)-2-methylpyrrolidine-2-carboxylic acid hydrochloride (23; 82.5 g, 498 mmol) was dissolved in a solvent mixture of acetonitrile/water (1:1, 1000 mL) and triethylamine (TEA, 210 mL, 1490 mmol) was added. Subsequently, di-tert-butyl dicarbonate (Boc2O, 120 g, 548 mmol) dissolved in acetonitrile (200 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The organic solvent was removed by evaporation under reduced pressure and 2M aqueous sodium hydroxide (300 mL) was added to the residue. The aqueous phase was extracted with ether (Et2O, 400 mL), cooled to 10 °C and the pH was adjusted to 5-6 by slow addition of 25% aqueous hydrochloric acid. 1M aqueous hydrochloric acid was then carefully added to pH=2 and the product precipitated. The precipitate was collected by filtration, washed with water (300 mL), and dried under high vacuum to give (S)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (24, 90.7 g) as a light gray solid. lc-MS: tR = 0.63 min; [M + H]+ = 230.24. | | References | [1] Tetrahedron Letters, 1996, vol. 37, # 20, p. 3441 - 3444
[2] Patent: WO2008/8551, 2008, A2. Location in patent: Page/Page column 34
[3] Patent: US2010/197654, 2010, A1. Location in patent: Page/Page column 57
[4] Organic Letters, 2011, vol. 13, # 22, p. 5964 - 5967
[5] Patent: WO2013/182972, 2013, A1. Location in patent: Page/Page column 110 |
| | N-Boc-alpha-methyl-L-proline Preparation Products And Raw materials |
| Raw materials | (S)-2-Methyl-2-pyrrolidinecarboxylicacid-->1,2-Pyrrolidinedicarboxylic acid, 2-methyl-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S)--->(S)-2-Methylproline-->L-Proline-->Di-tert-butyl dicarbonate-->1,2-Pyrrolidinedicarboxylic acid, 2-methyl-, 1-(1,1-dimethylethyl) ester, (2S)-, compd. with (αS)-α-methylbenzenemethanamine (1:1)-->Acetonitrile-->Water-->Triethylamine-->2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile |
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