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

HRID 10501

反応式

HRID 10501 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-881ac3f56ed04e33b46fda327ae9d93f
出典データセット
uspto-grants-2006_08
特許番号
US07094789B2

関連ノート

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