1,4-Dioxa-8-azaspiro(4.5)decane → 8-(3-Methyl-[1,2,4]thiadiazol-5-yl)-1,4-dioxa-8-aza-spiro[4.5]decane

HRID 451371ノート

反応式

HRID 451371 の反応式
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O:26]1[C:30]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:29][CH2:28][CH2:27]1.Cl[C:37]1[S:41][N:40]=[C:39]([CH3:42])[N:38]=1>O1CCOCC1.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:42][C:39]1[N:38]=[C:37]([N:33]2[CH2:34][CH2:35][C:30]3([O:29][CH2:28][CH2:27][O:26]3)[CH2:31][CH2:32]2)[S:41][N:40]=1

参加物

7

反応物 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazole

生成物 1

HCID 583979828-(3-Methyl-[1,2,4]thiadiazol-5-yl)-1,4-dioxa-8-aza-spiro[4.5]decane

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
130 °C

実験手順

To a prestirred solution (10 minutes at room temperature) of palladium(II) acetate (180 mg, 0.001 mmol) and 2-(dicyclohexylphosphino)biphenyl (572 mg, 0.002 mmol) in dioxane (10 mL) were added 1,4-dioxa-8-azaspiro(4,5)decane (1.3 mL, 10 mmol), 5-chloro-3-methyl-[1,2,4]thiadiazole (1.48 g, 11 mmol) and sodium tert-butylate (1.47 g, 15 mmol) and heated in the microwave at 130° C. for 15 minutes. The reaction mixture was diluted with half saturated brine, the aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue was purified by silica gel chromatography using ethyl acetate as eluent. The title compound was obtained as a light yellow solid (1.87 g, 77%).

後処理

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-7ccbc31a04fd4186be31720467f31f27
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

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