|
|
| | tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Basic information |
| Product Name: | tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate | | Synonyms: | tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate;6-oxo-2-azaspiro[3.3]heptane-2-carboxylate;2-Boc-6-hydroxy-2-aza-spi...;2-Boc-6-hydroxy-2-aza-spiro[3.3]heptane;6-Hydroxy-2-azaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester;2-Azaspiro[3.3]heptane-2-carboxylic acid, 6-hydroxy-, 1,1-diMethylethyl ester;6-Hydroxy-2-azaspiro[3.3]heptane, N-BOC protected;tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate, 2-(tert-Butoxycarbonyl)-6-hydroxy-2-azaspiro[3.3]heptane | | CAS: | 1147557-97-8 | | MF: | C11H19NO3 | | MW: | 213.27 | | EINECS: | | | Product Categories: | | | Mol File: | 1147557-97-8.mol | ![tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Structure](CAS2/GIF/1147557-97-8.gif) |
| | tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Chemical Properties |
| Melting point | 127-129℃ | | Boiling point | 316.6±42.0 °C(Predicted) | | density | 1.17 | | storage temp. | 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 14.84±0.20(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C11H19NO3/c1-10(2,3)15-9(14)12-6-11(7-12)4-8(13)5-11/h8,13H,4-7H2,1-3H3 | | InChIKey | UMXXHZDEAZUQKZ-UHFFFAOYSA-N | | SMILES | C1C2(CC(O)C2)CN1C(OC(C)(C)C)=O |
| | tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Usage And Synthesis |
| Uses | tert-Butyl 6-Hydroxy-2-azaspiro[3.3]heptane-2-carboxylate is a reactant used in the synthesis of pharmaceuticals such as CNS penetrant CXCR2 antagonists for the potential treatment of CNS demyelinating. | | Synthesis | Step 8: Synthesis of tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate
At 0 °C and under nitrogen protection, tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate (507 mg, 2.4 mmol) was dissolved in methanol (5.0 mL) and sodium borohydride (182 mg, 4.8 mmol) was added slowly. The reaction mixture was stirred at 0 °C for 30 min. After completion of the reaction, the solvent was concentrated in vacuum by rotary evaporator to give the crude product. Saturated sodium bicarbonate solution (30 mL) was added to the crude product and the aqueous phase was extracted with dichloromethane (4 x 30 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to afford tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (5 mg, 100% yield) as a white solid.1H NMR (300 MHz, CDCl3): δ 4.18 (m, 1H), 3.88 (d, 4H), 2.53 (m, 2H), 2.08 (m. 2H), 1.42 (s, 9H). | | References | [1] Patent: WO2013/13308, 2013, A1. Location in patent: Paragraph 00178-00180
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5663 - 5672
[3] Patent: CN106565706, 2017, A. Location in patent: Paragraph 0179; 0180; 0181
[4] Patent: EP3281942, 2018, A1. Location in patent: Paragraph 0105; 0106
[5] Patent: WO2018/133858, 2018, A1. Location in patent: Paragraph 00221 |
| | tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate Preparation Products And Raw materials |
|