Water → 6-Hydroxy-2-[3-hydroxymethyl-4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-(4-morpholinylmethyl)phenyl Ketone

HRID 1387121Notes

Reaction equation

HRID 1387121 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([C:17]2[C:18]3[CH:48]=[CH:47][C:46]([O:49]CC4C=CC=CC=4)=[CH:45][C:19]=3[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:24]([CH2:36][O:37][Si](C(C)(C)C)(C)C)[CH:23]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[OH2:57]>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([C:17]2[C:18]3[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][C:19]=3[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:24]([CH2:36][OH:37])[CH:23]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:11][CH2:12][O:57][CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 962WaterHCID 211827376-Benzyloxy-2-[3-t-butyldimethylsilyloxymethyl-4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-(1-pyrrolidinylmethyl)phenyl Ketone

Product 1

HCID 211827476-Hydroxy-2-[3-hydroxymethyl-4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-(4-morpholinylmethyl)phenyl KetoneYield 22%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

The (30.8 mg, 0.0381 mmol) 6-benzyloxy-2-[3-t-butyldimethylsilyloxymethyl-4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-methoxy-4-(1-pyrrolidinylmethyl)phenyl ketone (Part C) was dissolved in 0.5 mL of 1N tetrabutylammonium fluoride in THF. The solution was stirred at room temperature for 1 h. To the reaction mixture was added 1.0 mL of water and diluted with 15 mL of EtOAc. The layers were separated and the aqueous layer was extracted (1×10 mL) with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (silica gel, 80:17:3 THF-Hexanes-Et3N) afforded 5.7 mg (0.0082 mmol, 22%) of a yellow oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted (1×10 mL) with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (silica gel, 80:17:3 THF-Hexanes-Et3N)

Sources & evidence

ORD record
ord-cac3c9ec43ad4488ab9615ddde1fdf37
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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