Identification | Back Directory | [Name]
8-Methyl-1,4-dioxaspiro[4,5]decan-8-ol | [CAS]
66336-42-3 | [Synonyms]
8-Methyl-1,4-dioxaspiro[4,5]decan-8-ol 1,4-Dioxaspiro[4.5]decan-8-ol, 8-methyl- | [Molecular Formula]
C9H16O3 | [MDL Number]
MFCD11108667 | [MOL File]
66336-42-3.mol | [Molecular Weight]
172.22 |
Chemical Properties | Back Directory | [Melting point ]
70-71 °C | [Boiling point ]
267.7±40.0 °C(Predicted) | [density ]
1.14±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
15.18±0.20(Predicted) |
Hazard Information | Back Directory | [Uses]
8-Methyl-1,4-dioxaspiro[4.5]decan-8-ol is used in preparation of pyrrolopyridine derivatives and related compounds as BCL-2 inhibitors for treating neoplastic, autoimmune or neurodegenerative diseases. | [Synthesis]
Step 1: Synthesis of 8-methyl-1,4-dioxaspiro[4.5]decan-8-ol: 1,4-dioxaspiro[4.5]decan-8-one (7.8 g, 50.0 mmol) was dissolved in dry THF (75 mL) and cooled to -78 °C under argon protection. Methyl lithium solution (1.5 M in ether, 43.3 mL, 65.0 mmol) was added slowly, controlling the reaction temperature to not exceed -55 °C. After addition, the reaction mixture was continued to be stirred at -55 °C for 4 hours. Subsequently, the reaction system was slowly warmed to room temperature and the reaction was quenched with saturated NH4Cl solution. The organic layer was separated and concentrated in vacuum, and the resulting residue was purified by silica gel column chromatography (eluent ratio: ethyl acetate:petroleum ether = 1:9 to 1:3) to afford the target product, 8-methyl-1,4-dioxaspiro[4.5]decan-8-ol, as a white solid (6.8 g, yield: 80%). | [References]
[1] Canadian Journal of Chemistry, 1997, vol. 75, # 6, p. 656 - 664 [2] Patent: WO2014/9302, 2014, A1. Location in patent: Page/Page column 89 [3] Patent: US2015/158879, 2015, A1. Location in patent: Paragraph 0437; 0438 [4] Patent: US2016/200741, 2016, A1. Location in patent: Paragraph 0438-0439 [5] Patent: WO2008/119716, 2008, A1. Location in patent: Page/Page column 49 |
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