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Triethylamine → cis-8-Methyl-6-phenyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester

HRID 1714146
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HRID 1714146 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=[C:6]2[C:14]=1[CH2:13][C@H:12]1[C@@H:7]2[CH2:8][NH:9][CH2:10][CH2:11]1.CCN(CC)CC.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(Cl)Cl>[CH2:32]([O:31][C:29]([N:9]1[CH2:8][C@H:7]2[C@H:12]([CH2:13][C:14]3[C:6]2=[CH:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][C:2]=3[CH3:1])[CH2:11][CH2:10]1)=[O:30])[CH3:33]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16117678cis-8-Methyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

생성물 1

HCID 86611062cis-8-Methyl-6-phenyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester수율 71.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

To a solution of cis-8-methyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (22 mg, 0.084) in CH2Cl2 was added Et3N (43 mg, 0.42 mmol) followed by ethyl chloroformate (18 mg, 0.17 mmol). The reaction mixture was stirred at 20° C. for 2 h and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 9/1) to give cis-8-methyl-6-phenyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (20 mg, 0.060 mmol).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed in silica gel column (Hex/EtOAc 9/1)

출처 및 근거

ORD 기록
ord-1652b807604e4731b8fd7c61962a771d
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795436B2

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