Tetrabutylammonium Fluoride → HCID 66993280, compound

HRID 381494Notes

Reaction equation

HRID 381494 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:48])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C@@:34](O[Si](C(C)(C)C)(C)C)([OH:39])[CH2:35][N:36]([CH3:38])[CH3:37])=[CH:28][CH:27]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:48])/[CH:24]=[CH:25]/[C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][C@H:34]([OH:39])[CH2:35][N:36]([CH3:38])[CH3:37])=[CH:30][CH:31]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70107649HCID 70107649, compound

Product 1

HCID 66993280HCID 66993280, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. to a solution (E)-(R)-1-[1-(2,3-dihydrobenzofuran-5-yl)-1,3,4,9-tetrahydro-β-carbolin-2-yl]-3-(4-(2-(tertbutyldimethylsilanyloxy)-3-dimethylamino-2-hydroxy-propoxy)phenyl)propene-1-one (0.4 g, 0.6 mmol) in 50 mL of anhydrous THF was added tetrabutylammonium fluoride (0.6 mL, 1 equiv., 1 M in THF). The resulting mixture was stirred at rt for one day. Quenching with water, extraction with DCM, washing with brine, drying over MgSO4 and concentration in vacuo gave an oil. Recrystallization from iPrOH:H2O gave the title compound (0.2 g, 62%) as an off-white powder.

Workup

  1. customQuenching with water, extraction with DCM
  2. washwashing with brine
  3. dry with materialdrying over MgSO4 and concentration in vacuo
  4. customgave an oil
  5. customRecrystallization from iPrOH

Sources & evidence

ORD record
ord-6927370747d6473aa1a0e72bcd18490a
Source dataset
uspto-grants-2001_10
Patent number
US06306870B1

Reaction notes

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