Ammonium Chloride → HCID 71000664、化合物

HRID 1023431

反応式

HRID 1023431 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[CH:21]1([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH2:23][CH2:22]1.[NH4+].[Cl-]>C1COCC1.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][C:24]([CH:21]2[CH2:22][CH2:23]2)([OH:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 77029Cyclopropyl phenyl ketoneHCID 11063648tert-butyl N-(4-methylpyridin-2-yl)carbamateHCID 178418339Butyllithium

生成物 1

HCID 71000664HCID 71000664、化合物収率 82.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

(4-Methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (200 mg, 0.96 mmol) is dissolved in dry THF (10 mL) and it is cooled down to −78° C. After 1.6 M n-BuLi (3.0 mL, 4.8 mmol) is added at −78° C., the cooling bath is removed and the mixture is stirred at room temperature for 15 min. Then the reaction mixture is cooled down to −78° C. again and cyclopropyl-phenyl-methanone (0.68 mL, 4.8 mmol) is added. After the mixture is stirred for 30 min at −78° C., saturated NH4Cl aqueous solution (35 mL) is added and the reaction is warmed up to room temperature. EtOAc (70 mL) is added along with water (70 mL). The mixture is stirred for another 10 min and the aqueous layer is separated, extracted with EtOAc (2×35 ml). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 280 mg of the desired product.

後処理

  1. customthe cooling bath is removed
  2. temperatureThen the reaction mixture is cooled down to −78° C. again
  3. stirringAfter the mixture is stirred for 30 min at −78° C.
  4. temperaturethe reaction is warmed up to room temperature
  5. stirringThe mixture is stirred for another 10 min
  6. customthe aqueous layer is separated
  7. extractionextracted with EtOAc (2×35 ml)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica flash column chromatography

出典と根拠

ORDレコード
ord-74cea6fbb84e437e9ddb61a3993d0c1b
出典データセット
uspto-grants-2014_05
特許番号
US08722709B2

関連ノート

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