Water → Tert-Butyl 6-(1-methyl-1H-pyrazol-4-yl)-4-oxo-spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 38476

反応式

HRID 38476 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:21](=[CH:22][CH:23]=1)[O:20][C:7]1([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:24].[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.O>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][N:26]1[CH:30]=[C:29]([C:2]2[CH:3]=[C:4]3[C:21](=[CH:22][CH:23]=2)[O:20][C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:9][CH2:8]2)[CH2:6][C:5]3=[O:24])[CH:28]=[N:27]1

参加物

7

反応物 3

HCID 962WaterHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2794759tert-Butyl 6-bromo-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

生成物 1

HCID 57931011Tert-Butyl 6-(1-methyl-1H-pyrazol-4-yl)-4-oxo-spiro[chroman-2,4'-piperidine]-1'-carboxylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

tert-Butyl 6-bromo-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (1 g) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (682 mg) were dissolved in dioxane in a nitrogen atmosphere, and aqueous 2M Na2CO3 (10 ml) solution (3.8 mL) and tetrakis(triphenylphosphine)palladium (144 mg) were added thereto, and degassed. The reaction liquid was stirred overnight at 100° C., cooled to room temperature, then water was added thereto, and filtered through Celite. The filtrate was extracted with chloroform, and the organic layer was dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/EtOAc) to obtain the intended compound as a pale yellow solid.

後処理

  1. additionwere added
  2. customdegassed
  3. customThe reaction liquid
  4. temperaturecooled to room temperature
  5. filtrationfiltered through Celite
  6. extractionThe filtrate was extracted with chloroform
  7. dry with materialthe organic layer was dried with sodium sulfate
  8. customSodium sulfate was removed through filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe residue was purified through silica gel column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-67eb52c178e84a9ea08b3ca34d24cc0a
出典データセット
uspto-grants-2013_09
特許番号
US08524730B2

関連ノート

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