1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Benzo[d]isoxazol-3-yl-piperazine-1-carboxylic acid tert-butyl ester

HRID 271786

反応式

HRID 271786 の反応式
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][N:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27797803-Chloro-1,2-benzoxazole

生成物 1

HCID 592523164-Benzo[d]isoxazol-3-yl-piperazine-1-carboxylic acid tert-butyl ester収率 42%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 100 mg (0.65 mmol) of 3-chloro-1,2-benzisoxazole in pyridine (1 mL) was added 145 mg of piperazine-1-carboxylic acid tert-butyl ester (0.78 mmol) and 0.18 mL of DBU (0.78 mmol). The mixture was stirred at 100° C. overnight and then partitioned between EtOAC (50 mL) and water (20 mL) and separated. The aqueous layer was extracted with EtOAC (2×30 mL). The combined organic layers were then washed with water (25 mL), brine, dried over Na2SO4, and the solvent was removed under reduced pressure to give crude product. Purification by column chromatography (silica, 60-100% CH2Cl2/hexanes) gave 82 mg (42%) of the desired product as a light yellow solid. MS (electrospray): exact mass calculated for C16H21N3O3, 303.16; m/z found, 326.1 [M+Na]+. 1H NMR (CDCl3, 400 MHz): 7.68 (dt, J=8.02, 0.98 Hz, 1H), 7.52-7.44 (m, 2H), 7.24 (ddd, J=8.42, 6.46, 1.57 Hz, 1H), 3.66-3.61 (m, 4H), 3.56-3.49 (m, 4H), 1.49 (s, 9H).

後処理

  1. custompartitioned between EtOAC (50 mL) and water (20 mL)
  2. customseparated
  3. extractionThe aqueous layer was extracted with EtOAC (2×30 mL)
  4. washThe combined organic layers were then washed with water (25 mL), brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customto give crude product
  8. customPurification by column chromatography (silica, 60-100% CH2Cl2/hexanes)

出典と根拠

ORDレコード
ord-6fd1099501c54868937e6a852b7d364b
出典データセット
uspto-grants-2008_11
特許番号
US07452890B2

関連ノート

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