1-(1H-Pyrazol-1-yl)ethanone → HCID 117697480、化合物

HRID 1778477ノート

反応式

HRID 1778477 の反応式
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][C:15](=[O:17])[CH2:16][CH:9]1[CH2:10][O:11][CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.N1([C:33](=[O:35])[CH3:34])C=CC=N1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH:14]([C:33](=[O:35])[CH3:34])[C:15](=[O:17])[CH2:16][CH:9]1[CH2:10][O:11][CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 5492781-(1H-Pyrazol-1-yl)ethanoneHCID 2733832Lithium HexamethyldisilazideHCID 185070529-Boc-7-oxa-9-azabicyclo[3.3.1]nonan-3-one

生成物 1

HCID 117697480HCID 117697480、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (482 mg, 2 mmol) in THF (5 mL) was added LiHMDS (3 mL, 3 mmol) slowly at −78° C. After 15 mins, 1-pyrazol-1-yl-ethanone (264 mg, 2.4 mmol) was added, and the resulting mixture was stirred at −78° C. for 1 hour and then at room temperature for 1 hour. The reaction mixture was quenched with water, and then extracted with EA (20 mL×2). The organic layer was concentrated in vacuo. The residue was purified by flash chromatography (EA in PE 0%˜70%) to afford 6-acetyl-7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (compound AL) as light yellow oil (56 mg, 20%). LC/MS: calc'd 284 (MH+), exp 284 (MH+).

後処理

  1. waitat room temperature for 1 hour
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EA (20 mL×2)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe residue was purified by flash chromatography (EA in PE 0%˜70%)

出典と根拠

ORDレコード
ord-0d0ab5e5221e447793f1df53e3710fda
出典データセット
uspto-grants-2016_02
特許番号
US09266904B2

反応ノート

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