4-Benzylphenol → cis-1-(4-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane

HRID 965224

반응식

HRID 965224 반응식
[C:1]([O:5][C:6]([N:8]1[CH:10]2[CH2:11][C:12]3[C:17]([CH:9]12)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:18]([C:25]1[CH:26]=[CH:27][C:28]([O:31][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 2

HCID 75634-BenzylphenolHCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

생성물 1

HCID 18661294cis-1-(4-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane수율 38.7%

시약·촉매·용매 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)촉매HCID 6212Chloroform용매2회

실험 절차

The title compound was prepared in a similar manner to Preparation 18 from (±)N-tert-butoxycarbonyl-1,2-iminoindane (2 g, 8.7 mmol), 4-benzylphenol (1.59 g, 8.7 mmol), pyridinium p-toluenesulfonate (30 mg) and chloroform (50 ml). After a reaction time of 3 h, the reaction was diluted with chloroform (50 ml) then washed sequentially with saturated aq. sodium bicarbonate, water and brine. After drying over Na2 SO4, volatiles were removed in vacuo and the residue subjected to column chromatography on neutral alumina eluting with 10% diethyl ether in hexanes to afford the title compound (1.4 g) as a foam

후처리

  1. washthen washed sequentially with saturated aq. sodium bicarbonate, water and brine
  2. customAfter drying over Na2 SO4, volatiles
  3. customwere removed in vacuo

출처 및 근거

ORD 기록
ord-9646a20809e8443b91dcc89031ac23c6
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773463

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