Ammonium Chloride → HCID 65920243、化合物

HRID 540405ノート

反応式

HRID 540405 の反応式
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[O:14]=[C:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1.[Cl-].[NH4+]>O1CCCC1>[F:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:15]1([OH:14])[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:18]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 612591-Bromo-2-fluorobenzeneHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418918HCID 178418918、化合物

生成物 1

HCID 65920243HCID 65920243、化合物収率 14%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-25 °C

実験手順

3.1 ml (6.1 mmol) of a 2M solution of isopropylmagnesium chloride in tetrahydrofuran are added to a solution of 1.1 g (6.2 mmol) of 1-bromo-2-fluorobenzene in 4 ml of tetrahydrofuran, cooled beforehand to −25° C. After stirring for 30 minutes at −25° C., a solution of 0.65 g (3.7 mmol) of 3-oxo-1-(tert-butoxycarbonyl)azetidine in 7.5 ml of tetrahydrofuran is added. The reaction medium is stirred for 30 min and then a saturated aqueous solution of ammonium chloride is added. The organic compounds are extracted with a 1/1 heptane/ethyl acetate mixture. The organic phase is dried over magnesium sulphate and then filtered and evaporated. The crude product is purified by silica gel chromatography, elution being carried out with a 5/5 heptane/ethyl acetate mixture. 135 mg of 3-(2-fluorophenyl)-3-hydroxy-1-(tert-butoxycarbonyl)-azetidine are obtained in the form of a white solid with a yield of 14%.

後処理

  1. stirringThe reaction medium is stirred for 30 min
  2. extractionThe organic compounds are extracted with a 1/1 heptane/ethyl acetate mixture
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by silica gel chromatography, elution

出典と根拠

ORDレコード
ord-65acacb9d88a404f9b795e93e209cdc4
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

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