2-Nitrophenyl selenocyanate → rel-(3S,5S)-trans-7-Chloro-5-(2-cyclopropylethenyl)-1,5-dihydro-3-ethenyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

HRID 369750ノート

反応式

HRID 369750 の反応式
[N+](C1C=CC=CC=1[Se]C#N)([O-])=O.[Na].Br[CH2:15][CH2:16][C@@H:17]1[O:23][C@:22](/[CH:28]=[CH:29]/[CH:30]2[CH2:32][CH2:31]2)([C:24]([F:27])([F:26])[F:25])[C:21]2[CH:33]=[C:34]([Cl:37])[CH:35]=[CH:36][C:20]=2[NH:19][C:18]1=[O:38]>C1COCC1.C(O)C>[Cl:37][C:34]1[CH:35]=[CH:36][C:20]2[NH:19][C:18](=[O:38])[C@H:17]([CH:16]=[CH2:15])[O:23][C@:22](/[CH:28]=[CH:29]/[CH:30]3[CH2:32][CH2:31]3)([C:24]([F:25])([F:26])[F:27])[C:21]=2[CH:33]=1

参加物

6

反応物 3

HCID 1039312-Nitrophenyl selenocyanateHCID 5360545SodiumHCID 86755964rel-(3S,5S)-trans-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2 (3H)-one

生成物 1

HCID 66923228rel-(3S,5S)-trans-7-Chloro-5-(2-cyclopropylethenyl)-1,5-dihydro-3-ethenyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one収率 58.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a room temperature solution of 238 mg (1.05 mmol) of 2-nitrophenylselenocyanate in 3.0 mL of THF was added 9 mL of ethanol and 66 mg of sodium borchydride. After stirring 1.5 h, a solution of 153 mg of rel-(3S,5S)-trans-3-(2-bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one in 1.5 mL of dry THF and 5 mL of ethanol was added, and the resulting mixture was stirred at ambient temperature for 32 h. The reaction mixture was partitioned between water and ether, and the organic layer was washed with aqueous bicarbonate and brine, dried and evaporated. The crude product was purified by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes) to give 73 mg of the title compound as a pure solid which can be recrystallized from ethanol-hexanes: mp 165.5-166.5°; HRMS Calcd. for C17H16NO2F3Cl (M+H)+ : 358.082166. Found: 358.081658.

後処理

  1. stirringthe resulting mixture was stirred at ambient temperature for 32 h
  2. customThe reaction mixture was partitioned between water and ether
  3. washthe organic layer was washed with aqueous bicarbonate and brine
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-1968773e180641519c140450cf99f295
出典データセット
uspto-grants-2000_10
特許番号
US06140320

反応ノート

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