Sodium Carbonate → tert-Butyl 4-(3-phenylisoxazol-5-yl)piperidine-1-carboxylate

HRID 132327ノート

反応式

HRID 132327 の反応式
O[C:2]1([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:7]1([C:4]2[CH:3]=[C:2]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)[O:6][N:5]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 2

HCID 10340Sodium CarbonateHCID 59731869tert-Butyl 4-(5-hydroxy-3-phenyl-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate

生成物 1

HCID 59731907tert-Butyl 4-(3-phenylisoxazol-5-yl)piperidine-1-carboxylate収率 86%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

tert-Butyl 4-(5-hydroxy-3-phenyl-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate (320 mg, 0.92 mmol) was dissolved in methanol (10 mL). A solution of sodium carbonate (200 mg, 1.9 mmol) in water (10 mL) was added to the mixture. Reaction was stirred at reflux for 2 hours. Methanol was removed from the reaction mixture in vacuo. Remaining aqueous was extracted 2× ethyl acetate. Combined extracts were washed with brine. Organic layer was dried (magnesium sulfate), filtered, and concentrated. Title compound was obtained as off-white solid in 86% yield. (M−C4H8+H)+=273.1.

後処理

  1. customReaction
  2. temperatureat reflux for 2 hours
  3. customMethanol was removed from the reaction mixture in vacuo
  4. extractionRemaining aqueous was extracted 2× ethyl acetate
  5. washCombined extracts were washed with brine
  6. dry with materialOrganic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ff7e2411df184f0f8441eb3c215445d7
出典データセット
uspto-grants-2008_06
特許番号
US07384931B2

反応ノート

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