1-Azido-4-methylbenzene → 9-(p-Tolyl)-9-azabicyclo[6.1.0]nonane

HRID 2170130

반응식

HRID 2170130 반응식
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[N+]=[N-])=[CH:3][CH:2]=1.[CH:11]1=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]2[CH:12]3[CH:11]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:3][CH:2]=1

참가 물질

3

반응물 2

HCID 1374301-Azido-4-methylbenzeneHCID 638079Cyclooctene

생성물 1

HCID 764617309-(p-Tolyl)-9-azabicyclo[6.1.0]nonane

실험 절차

p-Tolyl azide (0.192 g, 1.44 mmol) and cis-cyclooctene (4.230 g, 38.4 mmol), and [(Me,EtTCPh)Fe(NCCH3)2](PF6)2 (0.0020 g, 0.0014 mmol) were used in the General S4 Catalytic Reaction described above yielding 0.302 g, 97.1%. 1H NMR (CDCl3, 499.74 MHz): δ 7.02 (d, J=8.5 Hz, 2H), 6.88 (d, J=8.0 Hz, 2H), 2.32 (dd, J1=13.5 Hz, J2=2.5 Hz, 2H), 2.28 (s, 3H), 2.05 (d, J=9.5 Hz, 2H), 1.65 (m, 4H), 1.50 (m, 6H). 13C NMR (CDCl3, 125.66 MHz): δ 153.08, 131.14, 129.41, 120.15, 43.73, 27.36, 27.20, 26.59, 20.77. GC/MS (m/z): 215.1. DART HR MS (m/z): [M+H]+216.1748 (found). C15H22N, 216.1752 (calcd).

후처리

  1. customabove yielding 0.302 g, 97.1%

출처 및 근거

ORD 기록
ord-8b8a650939dc4201a59ca83d4b3ac7f1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050589B2

연결된 노트

불러오는 중…