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 2296703노트

반응식

HRID 2296703 반응식
[N+](C1C=CC=CC=1[Se]C#N)([O-])=O.[BH4-].[Na+].Br[CH2:16][CH2:17][C@@H:18]1[O:24][C@:23](/[CH:29]=[CH: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](/[CH:29]=[CH:30]/[CH:31]3[CH2:33][CH2:32]3)([C:25]([F:26])([F:27])[F:28])[C:22]=2[CH:34]=1

참가 물질

6

반응물 3

HCID 1039312-Nitrophenyl selenocyanateHCID 4311764Sodium borohydrideHCID 86755964rel-(3S,5S)-trans-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethenyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2 (3H)-one

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

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 borohydride. 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.

후처리

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

출처 및 근거

ORD 기록
ord-8a2999f40b674ea58239146b2177a055
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489320B1

반응 노트

불러오는 중…