Thionyl Chloride → HCID 18516065, compound

HRID 1369457Notes

Reaction equation

HRID 1369457 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11](O)[CH:12]2[CH2:17][CH:16]3[N:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]2[CH2:14][CH2:15]3)[CH:6]=1>>[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([Cl:3])[CH:12]2[CH2:17][CH:16]3[N:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]2[CH2:14][CH2:15]3)[CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12074205HCID 12074205, compound

Product 1

HCID 18516065HCID 18516065, compound

Procedure

Thionyl chloride (1 mL) was added to ethyl 2-((3-pyridyl)hydroxymethyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate (100 mg, 0.362 mmol) and the mixture was refluxed for 2 h and cooled. The excess thionyl chloride was removed under vacuum to give ethyl 2-((3-pyridyl)chloromethyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate, which was dissolved in 30 ml of water:ethanol (1:1 v/v volume) and treated with wet Raney nickel (0.5 g) under a nitrogen atmosphere. The suspension was shaken under 50 psi of hydrogen in a Parr hydrogenation apparatus for 24 h and filtered through a pad of celite. The celite was washed with ethanol (50 mL) and the combined ethanol solutions were concentrated by rotary evaporation. The remaining aqueous solution was extracted with chloroform (3×50 mL). The combined chloroform extracts were dried over anhydrous potassium carbonate, filtered, and rotary evaporated. The residue was chromatographed on a Merck silica gel 60 (70-230 mesh) column, with chloroform:methanol (95:5) as eluant. This afforded ethyl 2-((3-pyridyl)methyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate (90 mg, 96%).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. temperaturecooled
  3. customThe excess thionyl chloride was removed under vacuum

Sources & evidence

ORD record
ord-7d605f68c4274233aafc05e3ad9466f1
Source dataset
uspto-grants-2003_06
Patent number
US06579878B1

Reaction notes

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