Ethanol → HCID 11256216, compound

HRID 2115199Notes

Reaction equation

HRID 2115199 reaction equation
[CH2:1]([N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][C:7](=[C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=1)[C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[CH2:8]2)[CH:2]=[CH2:3].B(Br)(Br)Br.C([O-])(O)=O.[Na+].C(O)C>ClCCl>[CH2:1]([N:4]1[CH:5]2[CH2:11][CH2:10][CH:9]1[CH2:8][C:7](=[C:12]([C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)[CH2:6]2)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 11175578HCID 11175578, compound

Product 1

HCID 11256216HCID 11256216, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 72 mg (0.20 mmol) of 8-allyl-3-[(3-methoxy-phenyl)-thiophen-3-yl-methylene]-8-aza-bicyclo[3.2.1]octane in 2 mL of dichloromethane at −78° C. was added 1.68 mL ([1 M] in DCM) of boron tribromide drop wise. The reaction solution was slowly warmed to room temperature over 1 hr and allowed to stir 3 hr at room temperature. After 3 hr, to the reaction solution was added 4 mL of a saturated solution of NaHCO3, and 4 mL of 20% ethanol in DCM. The aqueous phase was removed. The organic phase was washed with 4 mL of brine, dried over MgSO4, and concentrated. The concentrated sample was purified by reverse phase chromatography (20×100 mm J'sphere H-80 YMC column using a gradient of 0.1% TFA/water to 5% water/0.1% TFA/acetonitrile). The eluent corresponding to 3-[(8-allyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-thiophen-3-yl-methyl]-phenol was evaporated to yield 12 mg of the title compound as a white solid; MS m/z (MH+) 338.

Workup

  1. waitAfter 3 hr
  2. customThe aqueous phase was removed
  3. washThe organic phase was washed with 4 mL of brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe concentrated sample was purified by reverse phase chromatography (20×100 mm J'sphere H-80 YMC column
  7. customThe eluent corresponding to 3-[(8-allyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-thiophen-3-yl-methyl]-phenol was evaporated

Sources & evidence

ORD record
ord-4aaaf3051f0c4896b8e5f5afcd520523
Source dataset
uspto-grants-2008_10
Patent number
US07435822B2

Reaction notes

Loading…