N,N,N',N'-Tetramethylazodicarboxamide → N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine

HRID 10501

반응식

HRID 10501 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22]O)([CH3:16])([CH3:15])[CH3:14].N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:13]([O:17][C:18]([NH:19][CH2:20][CH2:21][CH2:22][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[Cl:1])=[O:24])([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 219799331-Chloroisoquinolin-5-ol

생성물 1

HCID 21979957N-(tert-butoxycarbonyl)-3-[(1-chloro-5-isoquinolyl)oxy]propylamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of 1-chloro-5-hydroxyisoquinoline (539 mg, synthesized according to the method described in a reference (Georgian, V. et al., J. Org. Chem., 27, 4571 (1962))), (3-hydroxypropyl)carbamic acid tert-butyl ester (1.58 g, Tokyo Kasei Kogyo) and 1,1′-azobis(N,N-dimethylformamide) (1.55 g) in tetrahydrofuran (8 ml) was added with tri(n-butyl)phosphine (2.24 ml) with ice cooling and stirred at room temperature for 24 hours. The deposited solid was removed by filtration, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (860 mg) as white powdery solid.

후처리

  1. customsynthesized
  2. customThe deposited solid was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThen, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-881ac3f56ed04e33b46fda327ae9d93f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094789B2

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