Boron tribromide → N-Trifluoroacetyl-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepine

HRID 84119노트

반응식

HRID 84119 반응식
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 22292800HCID 22292800, 화합물

생성물 1

HCID 22292790N-Trifluoroacetyl-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepine수율 95.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.506 g, 1.76 mmol) in dichloromethane (20 mL) was treated with BBr3 (4.1 mL of a 1.0M solution in CH2Cl2, 4.1 mmol) and stirred overnight while warming to 20 C. The excess BBr3 was quenched with water, and the resulting mixture was diluted with ether (200 mL), washed with Na2CO3 (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 0.460 g of a white solid foam. MS calculated for C13H14F3NO2+H: 274, observed: 274.

후처리

  1. temperaturewhile warming to 20 C
  2. customThe excess BBr3 was quenched with water
  3. additionthe resulting mixture was diluted with ether (200 mL)
  4. washwashed with Na2CO3 (100 mL) and brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b153befc247c4a9e873a22bb8aa9a4b1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846906B2

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