Tetrabutylammonium Fluoride → HCID 86604035, compound

HRID 1351990Notes

Reaction equation

HRID 1351990 reaction equation
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][CH2:19][N:20]([CH2:28][C@H:29]([OH:36])[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][CH2:19][N:20]([CH2:28][C@H:29]([OH:36])[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 86604036HCID 86604036, compound

Product 1

HCID 86604035HCID 86604035, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of tert-butyl [2-(4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)ethyl][(2R)-2-hydroxy-2-pyridin-3-ylethyl]carbamate (316 mg, 0.618 mmol) in tetrahydrofuran (5 mL) is added a 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran (927 μL, 1.5 equivalent), and the mixture is stirred at room temperature for 3 hours. Further, to the mixture is added a 1.0 M solution of tetrabutyl-ammonium fluoride in tetrahydrofuran (927 μL, 1.5 equivalent), and the mixture is stirred for 15 hours. The reaction mixture is concentrated under reduced pressure, and the obtained brown residue is purified by silica gel column (ammonia-chloroform:methanol=100:1→50:1→20:1) to give the title compound as oil (239 mg, yield: 97%).

Workup

  1. stirringthe mixture is stirred for 15 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe obtained brown residue is purified by silica gel column (ammonia-chloroform:methanol=100:1→50:1→20:1)

Sources & evidence

ORD record
ord-be6eb53df5a04cd79048cca57643504e
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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