Acetic Acid → HCID 59813153, compound

HRID 2115196Notes

Reaction equation

HRID 2115196 reaction equation
[C:1]1([C:7]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[C:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(OC)(OC)OC.ClCCl.CO>[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][N:15]1[CH:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][C:8](=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:16]1[CH:20]=[CH:19][S:18][CH:17]=1)[CH2:9]2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 107222-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11471554HCID 11471554, compound

Product 1

HCID 59813153HCID 59813153, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

To 100 mg (355 μmol) of 3-(phenyl-thiophen-3-yl-methylene)-8-aza-bicyclo[3.2.1]octane in 1 mL of trimethyl orthoformate was added 62 μL (533 μmol) of 2-methylbenzaldehyde, 173 mg (817 μmol) of sodium triacetoxyborohydride, 34 μL of glacial acetic acid at room temperature. The reaction mixture was allowed to stir overnight at room temperature. Next day, the crude was diluted with 1 mL of dichloromethane and 0.5 mL of methanol. The diluted suspension was filtered and the precipitates were washed with dichloromethane. The combined filtrates were 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 was evaporated to yield the title compound as a white solid; MS m/z (MH+) 386; 1H NMR 300 MHz (MeOD-d4) δ 6.86-7.51 (m, 12H), 4.26 (s, 2H), 4.05-4.11 (m, 2H), 2.03-2.89 (m, 11H).

Workup

  1. filtrationThe diluted suspension was filtered
  2. washthe precipitates were washed with dichloromethane
  3. concentrationThe combined filtrates were concentrated
  4. customThe concentrated sample was purified by reverse phase chromatography (20×100 mm J'sphere H-80 YMC column
  5. customThe eluent was evaporated

Sources & evidence

ORD record
ord-7b5627222f3d433e94fa7c12da319fa6
Source dataset
uspto-grants-2008_10
Patent number
US07435822B2

Reaction notes

Loading…