N-methoxy-N-methylcycloheptanecarboxamide → Cycloheptyl(3-pyridinyl)methanone

HRID 900762ノート

反応式

HRID 900762 の反応式
CON(C)[C:4]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[Li][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>CCOCC>[CH:6]1([C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

参加物

4

反応物 2

HCID 12094213N-methoxy-N-methylcycloheptanecarboxamideHCID 178418470HCID 178418470、化合物

生成物 1

HCID 65399931Cycloheptyl(3-pyridinyl)methanone

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

A solution of N-methoxy-N-methylcycloheptanecarboxamide (1.11 g, 6 mmol) in ether (10 ml) was added dropwise at −78° C. to a solution of 3-lithiopyridine (prepared by addition of BuLi (3.75 ml, 6 mmol) to 3-bromopyridine (0.58 ml, 6 mmol) in ether (25 ml) at −78° C.). The mixture was stirred for 2 hours at −78° C., quenched by addition of aqueous saturated NH4Cl, allowed to warm to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted 3 times with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (CH2Cl2), the cycloheptyl(3-pyridinyl)methanone 18 was obtained as a slightly yellow oil (490 mg, 40%).

後処理

  1. customquenched by addition of aqueous saturated NH4Cl
  2. temperatureto warm to room temperature
  3. additiondiluted with ether
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted 3 times with ether
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customAfter purification by chromatography on silica gel (CH2Cl2)

出典と根拠

ORDレコード
ord-0f24c4cbb8bd417592cd9710636e0e75
出典データセット
uspto-grants-2008_04
特許番号
US07361668B2

反応ノート

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