Tetrabutylammonium Fluoride → 3-(1H-indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1890376Notes

Reaction equation

HRID 1890376 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([Si](C(C)C)(C(C)C)C(C)C)[CH:16]=[CH:15]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[CH:15]3)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 685963853-(1-triisopropylsilanyl-1H-indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 685974533-(1H-indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(1-Triisopropylsilanyl-1H-indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester (1.1 g, 64% purity, 1.63 mmol) was dissolved in THF (20 ml). Tetrabutylammonium fluoride (3.25 ml, 1 molar solution in THF) was added and the reaction mixture was stirred for 5 minutes at room temperature. The reaction mixture was concentrated, and the residue was dissolved in H2O (50 ml) and diethyl ether (50 ml). The crude product was purified by silica gel chromatography with dichloromethane as eluent, yielding the purified product (275 mg, 51% for 2 steps).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in H2O (50 ml)
  3. customThe crude product was purified by silica gel chromatography with dichloromethane as eluent
  4. customyielding the purified product (275 mg, 51% for 2 steps)

Sources & evidence

ORD record
ord-dbf83e4eabc4486886ecb15c8037d6be
Source dataset
uspto-grants-2013_08
Patent number
US08507469B2

Reaction notes

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