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

HRID 597840ノート

反応式

HRID 597840 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f12ab60e993f4ff590b3bc2e032d02b0
出典データセット
uspto-grants-2011_03
特許番号
US07897593B2

反応ノート

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