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

HRID 965228Notes

Reaction equation

HRID 965228 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6212ChloroformSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-98ff5d53c8af47b6a5c91e12d7cf00e3
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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