Bromide ion → HCID 15196233, compound

HRID 1645822Notes

Reaction equation

HRID 1645822 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[Br-].[Cl-].[NH4+].C[C:14]1[CH:19]=[CH:18][C:17](COC(NNC(C2C=NC=CN=2)=O)=O)=[CH:16][CH:15]=1.C1C[O:37][CH2:36]C1>O>[OH:9][C:3]1([C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:37][CH3:36])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

Participants

7

Reactant 5

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 195073-QuinuclidinoneHCID 25517Ammonium ChlorideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamate

Product 1

HCID 15196233HCID 15196233, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-quinuclidinone (3.97 g, 31.7 mmol) in THF (15 mL) was added dropwise to a solution of 2-methoxyphenylmagneisum bromide [prepared from 2-bromoanisole (3.76 mL, 28.9 mmol), iodine (2 crystals) and magnesium (0.77 g, 31.7 mmol) in THF (10 mL)] cooled in an ice/water bath. After 3 h at room temperature a saturated aqueous solution of ammonium chloride (50 mL) was added. The resulting mixture (pH10) was diluted with H2O (50 mL) and extracted with dichloromethane (4×50 mL). The combined organic extracts were washed with brine, dried over magnesium sulphate and evaporated to a light yellow oil. The crude product was purified by chromatography through silica-gel using dichloromethane/methanol/ammonia (89:10:1) as eluent to give the title compound as a colourless oil (1.02 g); 1H NMR (360 MHz, CDCl3) δ 1.45-1.65 (3H, m), and 2.32 (1H, m, 5 and 8-CH2), 2.44 (1H, br, OH); 2.46 (1H, m, 4-CH), 2.81 (2H, t, J=8 Hz) and 2.93 (1H, m) and 3.10 (1H, m 6 and 7-CH2), 3.29 (1H, d, J=15 Hz, 2-CH), 3.40 (1H, d, J=15 Hz, 2-CH), 3.91 (3H, s, OME), 6.98 (2H, m, Ar-H), 7.27 (2H, m, Ar-H); m/z 233 (M+).

Workup

  1. temperaturecooled in an ice/water bath
  2. extractionextracted with dichloromethane (4×50 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to a light yellow oil
  6. customThe crude product was purified by chromatography through silica-gel

Sources & evidence

ORD record
ord-fffb005010134068be5f3991d8f1de7c
Source dataset
uspto-grants-1993_01
Patent number
US05177084

Reaction notes

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