Ammonium Chloride → (1S,2S)-2-{4-[(R)-5-Cyano-4-(4-hydroxy-2,6-dimethyl-phenyl)-indan-1-yloxy]-phenyl}cyclopropanecarboxylic acid ethyl ester

HRID 471439Notes

Reaction equation

HRID 471439 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]([C:27]4[C:32]([CH3:33])=[CH:31][C:30]([O:34][Si](C(C)(C)C)(C)C)=[CH:29][C:28]=4[CH3:42])[C:21]([C:25]#[N:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[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]([C:27]4[C:32]([CH3:33])=[CH:31][C:30]([OH:34])=[CH:29][C:28]=4[CH3:42])[C:21]([C:25]#[N:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86703878HCID 86703878, compound

Product 1

HCID 86703880(1S,2S)-2-{4-[(R)-5-Cyano-4-(4-hydroxy-2,6-dimethyl-phenyl)-indan-1-yloxy]-phenyl}cyclopropanecarboxylic acid ethyl esterYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1S,2S)-2-(4-{(R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-phenyl]-5-cyano-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester (500 mg, 0.86 mmol) is dissolved in 10 mL of tetrahydrofuran, a 1 M aqueous solution of tetrabutylammonium fluoride (2 mL, 2.00 mmol) is added and the reaction mixture is stirred at room temperature for 3 h. 2 mL of an ammonium chloride saturated aqueous solution is added and the reaction mixture is concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 100/01→50/50) to give the title compound (Yield: 310 mg).

Workup

  1. concentrationthe reaction mixture is concentrated under vacuum
  2. customThe crude product obtained
  3. customis purified by flash chromatography (cyclohexane/ethyl acetate 100/01→50/50)

Sources & evidence

ORD record
ord-9a60e37492cb4c548df1f7c716fd790f
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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