(R)-camphorsulfonic acid → (Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

HRID 2371481Notes

Reaction equation

HRID 2371481 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][N:23](C1CCCCO1)[OH:24].[C@@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][NH:23][OH:24]

Participants

4

Reactant 2

HCID 131278(R)-camphorsulfonic acidHCID 86745523(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-[2-((tetrahydropyran-2-yl) hydroxamino)ethyl]indene

Product 1

HCID 86745522(Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the indene intermediate from Step 3 (1 g, 2.35 mmol) and (1R)-(-)-10-camphorsulfonic acid (546 mg, 2.35 mmol) in methanol (30 mL) was refluxed for 3 hours. The methanol was evaporated, the residue dissolved in ethyl acetate and the solution washed successively with water, twice with saturated aqueous sodium bicarbonate, and with water. After drying over Na2SO4, the residue obtained on evaporation of the solvent was triturated with ether and filtered to obtain the title compound as a yellow solid, mp: dec 126° C. which was identical to the product obtained in Method A, Step 4.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe methanol was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washthe solution washed successively with water, twice with saturated aqueous sodium bicarbonate
  5. dry with materialAfter drying over Na2SO4
  6. customthe residue obtained on evaporation of the solvent
  7. customwas triturated with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0be2ff7e819e46f0b45c42c8f66d85dc
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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