Sodium Hydroxide → 7-Allyloxy8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1035145노트

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HRID 1035145 반응식
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:23])[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.[Cl-].[Na+].O>[CH2:20]([O:19][C:17]1[C:16]([Br:23])=[CH:15][C:9]2[CH:10]([CH:12]([CH3:13])[CH3:14])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:18]=1)[CH:21]=[CH2:22]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 22292818N-Trifluoroacetyl-7-allyloxy-8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 100191247-Allyloxy8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine수율 118.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

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온도
50 °C

실험 절차

A solution of N-trifluoroacetyl-7-allyloxy-8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.011 g, 0.026 mmol) in methanol (0.5 mL) was treated with of 15% aqueous NaOH (0.5 mL), and stirred for 3 hours at 50° C. The product mixture was diluted with brine (5 mL), extracted twice with EtOAc (5 mL), dried with MgSO4, and concentrated to give 0.010 g of a clear oil. 1H NMR (400 MHz, CD3OD) 7.09 (s, 1H), 6.62 (s, 1H), 5.94 (m, 1H), 5.32 (dd, 1H), 5.12 (dd, 1H), 4.46 (d, 2H), 3.19 (m, 1H), 3.05 (m, 2H), 2.66 (m, 1H), 2.5 (bm, 2H), 2.3-2.1 (m, 2H), 0.95 (d, 3H), 0.63 (d, 3H). MS calculated for C16H22BrNO+H: 324, observed: 324.

후처리

  1. extractionextracted twice with EtOAc (5 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3c13d66da3fe4e609f1b998378551901
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546378B2

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