Tetrabutylammonium Fluoride → HCID 86669453, compound

HRID 2041739Notes

Reaction equation

HRID 2041739 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[C:15][Si](C(C)C)(C(C)C)C(C)C)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=2)[CH2:6][C@@H:5]1[CH3:34])(=[O:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[CH:15])=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=2)[CH2:6][C@@H:5]1[CH3:34])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67207195HCID 67207195, compound

Product 1

HCID 86669453HCID 86669453, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,4R)-1-acetyl-2-methyl-N-(6-methyl-2-pyridinyl)-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 111) (0.226 g, 0.475 mmol) in tetrahydrofuran (THF) (5 mL) at room temperature was treated with TBAF (1N in THF, 0.570 mL, 0.570 mmol) and the resulting mixture was stirred at this temperature for 30 min then most of the solvent was removed in vacuo. The residue was partitioned between AcOEt and water and the layers were separated. The organic phase was washed with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 10 G silica cartridge (gradient:5 to 25% (20% MeOH in DCM) in DCM) gave (2S,4R)-1-acetyl-6-ethynyl-2-methyl-N-(6-methyl-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine as an orange foam.

Workup

  1. customat room temperature
  2. custommost of the solvent was removed in vacuo
  3. customThe residue was partitioned between AcOEt and water
  4. customthe layers were separated
  5. washThe organic phase was washed with water
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by SP4

Sources & evidence

ORD record
ord-da49fce4e7564c7dab6a67ef5bec7b01
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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