Triethylamine → Benzyl 1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

HRID 597840노트

반응식

HRID 597840 반응식
[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C1COCC1.CCOC(C)=O>[O:1]1[C:6]2([CH2:11][CH2:10][N:9]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:8][CH2:7]2)[O:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27372161,5-Dioxa-9-azaspiro(5.5)undecane

생성물 1

HCID 59022466Benzyl 1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate수율 68%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1,5-dioxa-9-aza spiro[5.5]undecane (15.0 g, 95.4 mmol) and triethylamine (17.6 mL, 126 mmol) in THF (140 mL) cooled to 0° C. was added dropwise a solution of benzyl chloroformate (14 mL, 97.5 mmol) dissolved in THF (30 mL). The resulting mixture was stirred at room temp for 18 h. After diluting with EtOAc, the mixture was washed with water and brine and dried (Na2SO4). Concentration gave yellow oil that was purified by flash chromatography eluting with 20%-50% EtOAc/hexane to give the title compound as colorless oil (18.9 g, 68% yield). 1H NMR (300 MHz, CDCl3) δ: 7.36-7.27 (5H, m), 5.09 (2H, s), 3.89-3.85 (4H, m), 3.51-3.47 (4H, m), 1.87-1.66 (6H, m). LCMS (M+H) calcd for C16H22NO4: 292.15; found: 292.00.

후처리

  1. washthe mixture was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationConcentration
  4. customgave yellow oil that
  5. customwas purified by flash chromatography
  6. washeluting with 20%-50% EtOAc/hexane

출처 및 근거

ORD 기록
ord-f12ab60e993f4ff590b3bc2e032d02b0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897593B2

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