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

HRID 965228ノート

反応式

HRID 965228 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)触媒HCID 6212Chloroform溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-98ff5d53c8af47b6a5c91e12d7cf00e3
出典データセット
uspto-grants-1998_06
特許番号
US05773463

反応ノート

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