تفاعل #160215
ord-4ff4a8cf9f464d6d9c7229379c5ccfbb
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1workup.STIRRINGthe reaction mixture was stirred for 3 hours
- 2ترشيحfiltered
- 3تركيزconcentrated in vacuo
- 4أخرىThe residue was purified by silica gel column chromatography
- 5أخرىto give the ether intermediate as pale yellow oil
- 6ترشيحThe reaction mixture was filtered
- 7تركيزconcentrated in vacuo
- 8workup.ADDITIONdiluted with ethyl acetate
- 9غسيلwashed with 1:1 3M NaOH/
- 10تجفيفaq. NaHCO3, dried over MgSO4
- 11ترشيحfiltered
- 12تركيزconcentrated in vacuo
الإجراء التجريبي
To [8-benzyl-10-(hydroxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone hydrochloride salt (43 mg, 0.09 mmol) in DMF (0.5 mL) was added sodium hydride (11 mg, 0.30 mmol) and the reaction mixture was stirred for 20 minutes. Iodoethane (30 μL, 0.38 mmol) was added and the reaction mixture was stirred for 3 hours, then diluted with EtOAc, filtered, concentrated in vacuo. The residue was purified by silica gel column chromatography using 10-100 EtOAc/hexanes eluent to give the ether intermediate as pale yellow oil. The oil was dissolved in methanol (0.6 mL), and Pd (5 mg, 0.004 mmol) and ammonium formate (27 mg, 0.44 mmol) were added and the reaction mixture was heated at 75° C. for 40 minutes. The reaction mixture was filtered, concentrated in vacuo, diluted with ethyl acetate, washed with 1:1 3M NaOH/sat. aq. NaHCO3, dried over MgSO4, filtered and concentrated in vacuo to give [10-(ethoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (25 mg, 74%) as a pale yellow oil. ESI-MS m/z calc. 390.5. Found 391.3 (M+1)+; Retention time: 1.17 minutes (3 min run).