Potassium Carbonate → tert-Butyl 2-hydroxyimino-7-azaspiro[3.5]nonane-7-carboxylate

HRID 336556ノート

反応式

HRID 336556 の反応式
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].O=[C:11]1[CH2:14][C:13]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH2:12]1>C(O)C>[OH:3][N:2]=[C:11]1[CH2:14][C:13]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH2:12]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

生成物 1

HCID 86660644tert-Butyl 2-hydroxyimino-7-azaspiro[3.5]nonane-7-carboxylate収率 78.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

0.58 g (8.36 mmol) of hydroxylamine hydrochloride and 1.15 g (8.36 mmol) of potassium carbonate are added to a solution of 1.00 g (4.18 mmol) of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (U.S. Pat. No. 6,498,159) in 60 mL of ethanol, and the mixture is then left stirring at room temperature for 12 hours. After evaporating off the solvent under reduced pressure, the residue is taken up in dichloromethane and water, the aqueous phase is separated out and extracted twice with dichloromethane, and the combined organic phases are dried over sodium sulfate. After evaporating off the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia. 0.831 g of pure product is thus obtained in the form of a white powder.

後処理

  1. customAfter evaporating off the solvent under reduced pressure
  2. customwater, the aqueous phase is separated out
  3. extractionextracted twice with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. customAfter evaporating off the solvent
  6. customthe residue obtained
  7. customis purified by chromatography on silica gel
  8. washeluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia

出典と根拠

ORDレコード
ord-1b3419c31bcd4f3c9dc10390fe969008
出典データセット
uspto-grants-2014_11
特許番号
US08889702B2

反応ノート

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