Sodium Hydroxide → 8-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1010750노트

반응식

HRID 1010750 반응식
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Br:21][C:14]1[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 22292803N-Trifluoroacetyl-8-bromo-7-isopropoxy-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 100175568-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine수율 76.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of N-trifluoroacetyl-8-bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.014 g, 0.035 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred overnight at 20 C. The product mixture was diluted with water (3 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (3 mL), dried with Na2SO4 and concentrated to give 0.008 g of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.24 (s, 1H), 6.64 (s, 1H), 4.48 (m, 1H), 2.98 (m, 3H), 2.87 (m, 3H), 1.36 (m, 6H), 1.30 (d, J=7 Hz, 3H). MS calculated for C14H20BrNO+H: 298, observed: 298.

후처리

  1. extractionextracted twice with EtOAc (5 mL)
  2. washthe combined organic phases were washed with brine (3 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-beeb5d1e42f847ccb90a165da2008709
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977329B2

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