Tetrabutylammonium Fluoride → HCID 86669452, compound

HRID 2041737Notes

Reaction equation

HRID 2041737 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][C:30]([CH3:33])=[CH:29][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][C:30]([CH3:33])=[CH:29][N:28]=2)[CH2:6][C@@H:5]1[CH3:34])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67207244HCID 67207244, compound

Product 1

HCID 86669452HCID 86669452, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,4R)-1-acetyl-2-methyl-N-(5-methyl-2-pyridinyl)-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 109) (135 mg, 0.284 mmol) in tetrahydrofuran (THF) (3 mL) at room temperature was treated with TBAF (1N in THF, 0.341 mL, 0.341 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-(5-methyl-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine (70 mg, 0.219 mmol, 77% yield) 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-e39666d90c6245eea9f49c0415fe47f6
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

Loading…