Tetrabutylammonium Fluoride → HCID 89544955, compound

HRID 2283425Notes

Reaction equation

HRID 2283425 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][NH:9][C@@H:10]([C:13]1[C:14]([F:28])=[C:15]([C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[C:16]([Cl:19])=[CH:17][CH:18]=1)[CH2:11][CH3:12])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:10]([NH:9][CH2:8][CH2:7][OH:6])[CH2:11][CH3:12])=[C:14]([F:28])[C:15]=1[C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89544920HCID 89544920, compound

Product 1

HCID 89544955HCID 89544955, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To (3-{(R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethylamino]-propyl}-6-chloro-2-fluoro-phenyl)-pyridin-3-yl-methanone (0.176 g, 0.39 mmol) in THF (3 ml) at 0° C. added TBAF [1M] (90.43 ml, 0.43 mmol) dropwise stirred at 0° C. for 1 hour, diluted with water, THF evaporated off and reaction mixture extracted with DCM. The organic phase was separated and dried (Na2SO4), filtered and concentrated, purified by Prep HPLC to give 2-{[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]amino}ethan-1-ol (0.129 g).

Workup

  1. customevaporated off
  2. customreaction mixture
  3. extractionextracted with DCM
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by Prep HPLC

Sources & evidence

ORD record
ord-7910318dca704e2790daa961eefab864
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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