HCID 18665758, compound → HCID 18665759, compound

HRID 399253Notes

Reaction equation

HRID 399253 reaction equation
[C:1]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[C@@H:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[C@H:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[C@H:19]1[C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])([O:3]C(C)(C)C)=[O:2]>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[C:1]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[C@@H:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[C@H:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[C@H:19]1[C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])([OH:3])=[O:2]

Participants

5

Reactant 1

HCID 18665758HCID 18665758, compound

Product 1

HCID 18665759HCID 18665759, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 7519AnisoleCatalystHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl(1S,2R,3S)-3-(2-carbo-tert-butoxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (765 mg, 1.24 mmol) was dissolved in TFA (5 ml) containing a few drops of anisole. The reaction mixture was stirred at RT for 20 min. The solvent was eliminated, the residue was diluted with ethyl acetate, washed with water, brine and dried (MgSO4 anhyd.), filtered and evaporated. The product was purified by column chromatography to provide the title compound (575 mg, 83%) as a colorless oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4 anhyd.)
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-2d061057719540e0b498b537530c88b8
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

Loading…