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

HRID 546290노트

반응식

HRID 546290 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9f4b224bbc4a4d959a9abd431fadaba7
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935830B2

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