Tetrabutylammonium Fluoride → N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamide

HRID 1351926Notes

Reaction equation

HRID 1351926 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:39][Si](CC)(CC)CC)[CH2:16][NH:17][C@H:18]([CH3:38])[CH2:19][C:20]2[C:28]3[C:23](=[C:24]([O:29][CH2:30][C:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:32])[CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH2:36]([N:33]([CH2:34][CH3:35])[C:31](=[O:32])[CH2:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[NH:22][CH:21]=[C:20]2[CH2:19][C@H:18]([NH:17][CH2:16][C@H:15]([OH:39])[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 694597782-[3-((2R)-2-{2-[4-(tert-butyl-dimethylsilyloxy)phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide

Product 1

HCID 69458605N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamideYield 56.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[3-((2R)-2-{2-[4-(tert-butyldimethylsilyloxy)-phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}-propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide (40 mg, 0.060 mmol) and TBAF (261 mg, 1 mmol) in tetrahydrofuran (1 mL) is stirred at room temperature for 8 hours. After concentrated, the resultant is purified by preparative TLC (thickness: 0.5 mm, methanol/(a saturated ammonia solution in chloroform)=1/10), extracted with saturated aqueous sodium hydrogen carbonate solution/chloroform. The organic layer is dried over sodium sulfate, and concentrated to give the desired N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamide (15 mg, yield: 55%).

Workup

  1. concentrationAfter concentrated
  2. customthe resultant is purified by preparative TLC (thickness
  3. extraction0.5 mm, methanol/(a saturated ammonia solution in chloroform)=1/10), extracted with saturated aqueous sodium hydrogen carbonate solution/chloroform
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4ead536428142fcb7dd15771569fecc
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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