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(2-Bromo-Pyridin-3-Yl)-Carbamic Acid Tert-Butyl Ester → Tert-butyl 2-(hydroxy(1-(3-(trifluoromethyl)phenyl)cyclobutyl)methyl)-pyridin-3-ylcarbamate

HRID 1620996
ノート
印刷プレビュー

反応式

HRID 1620996 の反応式
Br[C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([C:29]2([CH:33]=[O:34])[CH2:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1>C1COCC1>[OH:34][CH:33]([C:29]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=2)[CH2:30][CH2:31][CH2:32]1)[C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14177127(2-Bromo-Pyridin-3-Yl)-Carbamic Acid Tert-Butyl EsterHCID 895247361-(3-(Trifluoromethyl)phenyl)cyclobutanecarbaldehydeHCID 178418339Butyllithium

生成物 1

HCID 89524814Tert-butyl 2-(hydroxy(1-(3-(trifluoromethyl)phenyl)cyclobutyl)methyl)-pyridin-3-ylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of Example 120A (400 mg, 1.465 mmol) in THF (5 mL) was added n-BuLi (3.08 mmol) at −78° C. The resulting solution was stirred at about −78° C. for about 1 hour and then a solution of Example 120C (365 mg, 1.611 mmol) in 10 mL of THF was added. The temperature was warmed to room temperature, stirred for another 1 hour, quenched with 10 mL of water, and extracted with ethyl acetate. The organic layer was washed with brine, and the combined organic phases were dried over sodium sulfate, filtered, and concentrated to give the desired crude product, which was used for next step without further purification. LC-MS: m/z (M+H) 439.

後処理

  1. temperatureThe temperature was warmed to room temperature
  2. stirringstirred for another 1 hour
  3. customquenched with 10 mL of water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialthe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4e1f97c4296c4a69bf136b31f4d6e16d
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772500B2

反応ノート

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