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| | TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Basic information |
| | TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Chemical Properties |
| Boiling point | 339.8±15.0 °C(Predicted) | | density | 1.029 | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Low-Melting Solid | | pka | 15.16±0.10(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C13H25NO3/c1-13(2,3)17-12(16)14-8-6-11(7-9-14)5-4-10-15/h11,15H,4-10H2,1-3H3 | | InChIKey | OXPWHPCCUXESFQ-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC(CCCO)CC1 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39 | | Hazard Note | Irritant | | HS Code | 2933399990 |
| | TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Usage And Synthesis |
| Uses | tert-Butyl 4-(3-Hydroxypropyl)piperidine-1-carboxylate is a reagent in the preparation of 1-alkyloxy-2-methoxy-4-nitrobenzene fragments: potent human glutaminyl cyclase inhibitors. | | Synthesis | The general procedure for the synthesis of N-BOC-4-(3'-hydroxypropyl)-piperidine from 3-(4-piperidinyl)-1-propanol and di-tert-butyl dicarbonate was as follows:
1. Di-tert-butyl dicarbonate (3.66 g, 16.8 mmol) was slowly added to a stirring solution of anhydrous dichloromethane (20 mL) of 3-(4-piperidinyl)-1-propanol (1.60 g, 11.2 mmol) under nitrogen protection and the reaction was carried out at ambient temperature.
2. The resulting reaction mixture was stirred continuously for 2 hours.
3. Upon completion of the reaction, the mixture was purified directly by silica gel column chromatography with the eluent being methanol in dichloromethane (0-3% gradient).
4. The target fraction was collected to afford N-BOC-4-(3'-hydroxypropyl)-piperidine as a clear oil (2.40 g, 88% yield). | | References | [1] Organic Letters, 2002, vol. 4, # 4, p. 549 - 552
[2] Patent: US2008/306082, 2008, A1. Location in patent: Page/Page column 5-6
[3] Patent: US6235731, 2001, B1
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 5, p. 783 - 794
[5] Tetrahedron, 1999, vol. 55, # 39, p. 11619 - 11639 |
| | TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Preparation Products And Raw materials |
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