(1S,2S)-2-{4-[(R)-4-(4-Benzyloxy-phenoxy)-7-fluoro-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester → (1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

HRID 625688Notes

Reaction equation

HRID 625688 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([O:33]CC5C=CC=CC=5)=[CH:29][CH:28]=4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 118093741(1S,2S)-2-{4-[(R)-4-(4-Benzyloxy-phenoxy)-7-fluoro-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester2×

Product 1

HCID 118093735(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

(1S,2S)-2-{4-[(R)-4-(4-Benzyloxy-phenoxy)-7-fluoro-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester (Intermediate 6, 0.76 g, 1.3 mmol) is dissolved in 1:1 MeOH/ethyl acetate (20 mL) and hydrogenated at 2 Bar for 1 hour using 10% palladium on carbon as the catalyst. The mixture is filtered through CELITE filter aid and the solvent removed under vacuum the title compound. (Yield 0.60 g). LC (METHOD 6): tR=0.64 min; Mass spectrum (ES+): m/z=449 [M+H]+.

Workup

  1. filtrationThe mixture is filtered through CELITE
  2. filtrationfilter aid
  3. customthe solvent removed under vacuum the title compound

Sources & evidence

ORD record
ord-975d16e7d0cc47b583a7298dade4f7f9
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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