2-Nitrophenyl selenocyanate → rel-(3S,5S)-7-Chloro-5-(2-cyclopropylethynyl)-1,5-dihydro-3-ethen yl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

HRID 369748ノート

反応式

HRID 369748 の反応式
[N+](C1C=CC=CC=1[Se]C#N)([O-])=O.[BH4-].[Na+].Br[CH2:16][CH2:17][CH:18]1[O:24][C:23]([C:29]#[C:30][CH:31]2[CH2:33][CH2:32]2)([C:25]([F:28])([F:27])[F:26])[C:22]2[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:21]=2[NH:20][C:19]1=[O:39]>C1COCC1.C(O)C>[Cl:38][C:35]1[CH:36]=[CH:37][C:21]2[NH:20][C:19](=[O:39])[C@H:18]([CH:17]=[CH2:16])[O:24][C@:23]([C:29]#[C:30][CH:31]3[CH2:33][CH2:32]3)([C:25]([F:26])([F:27])[F:28])[C:22]=2[CH:34]=1

参加物

6

反応物 3

HCID 1039312-Nitrophenyl selenocyanateHCID 4311764Sodium borohydride2 回HCID 183873743-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

生成物 1

HCID 56994752rel-(3S,5S)-7-Chloro-5-(2-cyclopropylethynyl)-1,5-dihydro-3-ethen yl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

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 409 mg (1.8 mmol) of 2-nitrophenylselenocyanate in 5.0 mL of THF was added 16 mL of ethanol and 90 mg of sodium borohydride. After stirring 1 h, a solution of 260 mg of rel-3S,5S)-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one in 1.5 mL of dry THF and 8 mL of ethanol was added, and the resulting mixture was stirred at ambient temperature for 2 h, at which time an additional 20 mg of sodium borohydride was added and stirring was continued for an additional 2 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 130 mg of the title compound as a pure solid: HRMS: Calcd. for C17H14NO2F3Cl (M+H)+ : 354.0508. Found: 354.0487.

後処理

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for an additional 2 h
  4. customThe reaction mixture was partitioned between water and ether
  5. washthe organic layer was washed with aqueous bicarbonate and brine
  6. customdried
  7. customevaporated
  8. 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-3b92645894154340bb2677abb054b1b4
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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