Triethylamine → N-Ethylcarbamate 6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508501ノート

反応式

HRID 508501 の反応式
[CH2:1]([NH:3][C:4](=[O:6])[O-:5])[CH3:2].O[C:8]1[C:9]([Cl:21])=[CH:10][C:11]2[CH:12]([CH3:20])[CH:13]3[CH2:17][NH:16][CH2:15][CH:14]3[C:18]=2[CH:19]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC>CO.CS(C)=O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([NH:3][C:4](=[O:5])[O-:6])[CH3:2].[Cl:21][C:9]1[CH:8]=[CH:19][C:18]2[CH:14]3[CH2:15][NH:16][CH2:17][CH:13]3[CH:12]([CH3:20])[C:11]=2[CH:10]=1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

生成物 1

HCID 86602846N-Ethylcarbamate 6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole収率 35%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a mixture of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole, o-trifluoromethanesulfonate (60 mg, 0.14 mmol), palladium(II) acetate (6 mg, 0.028 mmol) and 1,3-bis(diphenylphosphino) propane (12 mg, 0.035 mmol) in MeOH (0.5 mL) and DMSO (0.5 mL) was added Et3N (0.2 mL, 1.4 mmol). The resulting mixture was stirred for 2 hours at 80° C. then cooled to room temperature. The reaction mixture was diluted with EtOAc (5 mL) and then washed with H2O (2 mL). The organic extract was dried over MgSO4 and concentrated to afford 15 mg (35% yield) of the subtitle compound, which was used without further purification. MS calculated for C15H18ClNO2+H: 280, observed: 280.

後処理

  1. temperaturethen cooled to room temperature
  2. washwashed with H2O (2 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-72fb40f89c67440f954fea5a4c96a621
出典データセット
uspto-grants-2015_08
特許番号
US09096520B2

反応ノート

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