Phenol → (+/-)cis-1-Phenoxy-2-tert-butoxycarbonylaminoindane

HRID 965228

반응식

HRID 965228 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].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:24]([C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@@H:10]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 2

HCID 996PhenolHCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

생성물 1

HCID 18661301(+/-)cis-1-Phenoxy-2-tert-butoxycarbonylaminoindane수율 85.1%

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 (3 g, 13 mmol), phenol (1.22 g, 13 mmol), pyridinium p-toluenesulfonate (50 mg) and chloroform (100 ml). After a reaction time of 3 h, the reaction was diluted with chloroform (100 ml) then washed sequentially with saturated aq. sodium bicarbonate, water and brine. After drying over sodium sulfate, volatiles were removed in vacuo and the residue subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford a light brown solid which was recrystallised to afford the title compound (3.6 g) as a white solid m.p. 99°-101° C. (from diethyl ether-hexanes).

후처리

  1. washthen washed sequentially with saturated aq. sodium bicarbonate, water and brine
  2. dry with materialAfter drying over sodium sulfate, volatiles
  3. customwere removed in vacuo
  4. customto afford a light brown solid which
  5. customwas recrystallised

출처 및 근거

ORD 기록
ord-98ff5d53c8af47b6a5c91e12d7cf00e3
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773463

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