2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER CAS 170491-63-1
2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Basic information
| Product Name: | 2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER |
| Synonyms: | AKOS 92835;2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-N-BOC-2-HYDROXYMETHYLPYRROLIDINE;tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate;(±)-1-Boc-pyrrolidine-2-Methanol;1-Boc-(2-HydroxyMethyl)pyrrolidine;N-(tert-Butoxycarbonyl)pyrrolidine-2-methanol;N-Boc-2-pyrrolidineMethanol |
| CAS: | 170491-63-1 |
| MF: | C10H19NO3 |
| MW: | 201.26 |
| EINECS: | |
| Product Categories: | pharmacetical |
| Mol File: | 170491-63-1.mol |
2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties
| Melting point | 52-54℃ |
| Boiling point | 290℃ |
| density | 1.084 |
| Fp | 129℃ |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | soluble in Methanol |
| pka | 14.77±0.10(Predicted) |
| form | powder to crystal |
| color | White to Almost white |
| InChIKey | BFFLLBPMZCIGRM-UHFFFAOYSA-N |
| CAS DataBase Reference | 170491-63-1 |
Safety Information
| Risk Statements | 36/37/38 |
| Safety Statements | 26-37 |
| HS Code | 29339900 |
| Uses | N-(tert-Butoxycarbonyl)pyrrolidine-2-methanol is used to prepare 1,3-thiazolidin-2-imines derivatives as inhibitors of nitric oxide synthase. |
| Synthesis | 24424-99-5 498-63-5 170491-63-1 Step 1. Synthesis of tert-butyl 2-hydroxymethylpyrrolidine-1-carboxylatePyrrolidine-2-methanol (0.300 g, 1.98 mmol) was dissolved in dichloromethane (5.0 mL) and di-tert-butyl dicarbonate (0.650 g, 1.98 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the residue was purified by post-processing using Isco Combi-Flash Companion column chromatography (eluent: dichloromethane solution in 0-10% methanol) to afford tert-butyl 2-hydroxymethylpyrrolidine-1-carboxylate (0.590 g, 98% yield).1H NMR (CDCl3, 300 MHz) δ 4.78 (br d, 1H), 4.05-3.90 (br, 1H), 3.67-3.53 (m, 2H), 3.49-3.41 (m, 1H), 3.34-3.26 (m, 1H), 2.00 (dddd, 1H), 1.85-1.72 (m, 2H). 1.60-1.50 (m, 1H), 1.46 (s, 9H). |
| References | [1] Patent: US2017/253569, 2017, A1. Location in patent: Paragraph 0994-0995 [2] Tetrahedron, 2005, vol. 61, # 10, p. 2631 - 2643 [3] Patent: US2016/168090, 2016, A1. Location in patent: Paragraph 0823-0824 [4] Patent: WO2011/22508, 2011, A2. Location in patent: Page/Page column 59; 60 [5] Patent: EP2202223, 2010, A1. Location in patent: Page/Page column 72-73 |
2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Preparation Products And Raw materials
| Raw materials | 1-Boc-3-hydroxymethylpyrrolidine-->homoproline-->D(-)Prolinol-->2-FORMYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER-->1-N-BOC-2,3-DIHYDRO-PYRROLE-->Methyl 1-Boc-5-oxopyrrolidine-2-carboxylate-->2-(Hydroxymethyl)pyrrolidine-->carbon monoxide-->Di-tert-butyl dicarbonate-->DL-Proline-->L-(+)-Prolinol-->Bromochloromethane-->1-Boc-Pyrrolidine-->BOC-L-Proline |
| Preparation Products | 1-Methylpyrrolidine-2-methanol |
