Dimethylformamide → HCID 59486383、化合物

HRID 32080ノート

反応式

HRID 32080 の反応式
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN([CH:28]=[O:29])C>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:28]=[O:29])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 10064926tert-butyl N-(6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)carbamateHCID 178418339Butyllithium

生成物 1

HCID 59486383HCID 59486383、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

(6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (Step C) (1.080 g, 3.311 mmol) was dissolved in THF (30 mL) and cooled to −78° C. n-Butyllithium (2.5 M) (3.311 mL, 8.276 mmol) was added drop-wise to the stirred solution. The reaction was stirred at −78° C. for 30 min and DMF (1.282 mL, 16.55 mmol) was added drop-wise and the mixture was slowly warmed to RT overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude material, which was purified by flash column chromatography to furnish the pure title compound. MS (APCI pos) 217 (M-t-Bu).

後処理

  1. additionwas added drop-wise to the stirred solution
  2. temperaturethe mixture was slowly warmed to RT overnight
  3. customThe reaction was quenched with saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-fea7335b68e84aff8f79d6203751b877
出典データセット
uspto-grants-2008_09
特許番号
US07425631B2

反応ノート

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