tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate

HRID 459830ノート

反応式

HRID 459830 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:58]([O:62][C:63]([N:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1)=[O:64])([CH3:61])([CH3:60])[CH3:59].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:58]([O:62][C:63]([N:65]1[CH2:70][CH2:69][N:68]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)[CH2:67][CH2:66]1)=[O:64])([CH3:61])([CH3:59])[CH3:60]

参加物

8

反応物 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 7364875-BromoisoquinolineHCID 23676156Sodium t-butoxide

生成物 1

HCID 21070949tert-Butyl 4-(isoquinolin-5-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

5-Bromoisoquinoline (1.37 g) from Step 1 was dissolved in 10 mL of toluene. To this solution was added palladium acetate (74 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (205 mg), 1-(tert-butoxycarbonyl)piperazine (1.29 g) and sodium tert-butoxide (885 mg). This reaction mixture was heated to 100° C. for 8 hours and then allowed to cool to room temperature. The cooled reaction mix was diluted with ethyl acetate (EtOAc) and washed with water, and the organic layer was separated, dried over magnesium sulfate (MgSO4), and concentrated in vacuo. The resulting residue was chromatographed to yield 4-isoquinoline-5-yl-piperazine-1-carboxylic acid tert-butyl ester as 1.5 g of a white solid.

後処理

  1. temperatureto cool to room temperature
  2. customThe cooled reaction
  3. additionmix
  4. washwashed with water
  5. customthe organic layer was separated
  6. dry with materialdried over magnesium sulfate (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was chromatographed

出典と根拠

ORDレコード
ord-61939400dbce484b9a70d39c46e1a9e2
出典データセット
uspto-grants-2007_03
特許番号
US07196088B2

反応ノート

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