Boron trifluoride etherate → HCID 9943474, compound

HRID 1760634Notes

Reaction equation

HRID 1760634 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([CH:12]3[CH2:17][CH2:16][N:15]=[C:14]([CH3:18])[CH2:13]3)[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(F)(F)F.[CH3:23]COCC.[Li]C>C1COCC1>[CH3:18][C:14]1([CH3:23])[CH2:13][CH:12]([C:9]2[S:8][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=3[CH:10]=2)[CH2:17][CH2:16][NH:15]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 11459609HCID 11459609, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 9943474HCID 9943474, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude 4-(4-methoxybenzo[b]thiophen-2-yl)-2-methyl-3,4,5,6-tetrahydropyridine (2.19 g, 8.44 mmol) in THF (38 mL) cooled to −78° C. in a dry ice/acetone bath, was added dropwise BF3.Et2O (48%) (3.34 mL, 12.6 mmol) via a syringe. After stirring ten minutes, the solution was treated with 24.1 mL (33.77 mmol) of 1.4 M MeLi. The mixture was stirred for 16 h, then quenched with 100 mL of saturated aqueous NH4Cl and 50 mL of H2O. The mixture was then extracted with CH2Cl2 (3×100 mL). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography [2.5 to 7% (2.0 M NH3 in MeOH)/CH2Cl2] to give the title compound as an orange oil (0.713 g, 30%). IR (KBr) 2936, 1571, 1471, 1259, 1049 cm1. Ion Spray MS 276.2 (M+H)+. [α]D=0 (c 0.578, MeOH). C16H21NOS.0.1H2O.0.1 CH2Cl2

Workup

  1. stirringThe mixture was stirred for 16 h
  2. customquenched with 100 mL of saturated aqueous NH4Cl and 50 mL of H2O
  3. extractionThe mixture was then extracted with CH2Cl2 (3×100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography [2.5 to 7% (2.0 M NH3 in MeOH)/CH2Cl2]

Sources & evidence

ORD record
ord-27bd322de0bb413bad2a1a9161cbed9c
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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