Lithium Hydroxide → Tert-butyl 1-oxo-8-azaspiro(4.5)decane-8-carboxylate

HRID 8749

반응식

HRID 8749 반응식
COC([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:6]1=[O:22])=O.[OH-].[Li+]>C(O)C.O1CCCC1.O>[O:22]=[C:6]1[C:7]2([CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH2:8][CH2:9][CH2:5]1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 219838978-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate

생성물 1

HCID 10848487Tert-butyl 1-oxo-8-azaspiro(4.5)decane-8-carboxylate수율 67.5%

시약·촉매·용매 1

HCID 18504229Ethanol tetrahydrofuran water용매

반응 조건

온도
90 °C

실험 절차

To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (9.41 g).

후처리

  1. additionwas added
  2. temperatureto cool
  3. concentrationwas then concentrated
  4. dissolutiondissolved in water
  5. extractiondichloromethane, and extracted three times with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford 11.4 g
  11. customThe residue was purified by flash chromatography
  12. washeluting with 20–30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-279bb325608143949a9c5045f8750794
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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