Potassium Carbonate → 9-(Benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41556

反応式

HRID 41556 の反応式
Cl.[C:2]1(=[O:13])[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].Cl[C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1>CN(C=O)C>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[N:10]1[CH2:11][CH2:12][C:7]2([C:2](=[O:13])[NH:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][CH2:9]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 450742882,9-Diazaspiro(5.5)undecan-1-one hydrochloride

生成物 1

HCID 672537129-(Benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To the stirred solution of 2,9-diazaspiro[5.5]undecan-1-one hydrochloride [1187173-73-4] (100 mg, 0.49 mmol) in DMF (3 mL) was added K2CO3 (203 mg, 1.47 mmol) and 2-chloro benzoxazole [615-18-9] (82.8 mg, 0.54 mmol). The mixture was heated at 60° C. for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the crude mixture water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to obtain a yellow solid which was washed with diethyl ether and n-pentane to yield the title compound as solid (100 mg, 72%). [LCMS RtF=0.36 min, [M+H]+=286.1]

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. additionTo the crude mixture water was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a yellow solid which
  9. washwas washed with diethyl ether and n-pentane

出典と根拠

ORDレコード
ord-7d8c0276c0d2440aabcc1643f268cfba
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

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