8,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane → 3-(4-Methoxy-benzyl)-3-aza-bicyclo[3.2.1]octan-8-one

HRID 1295498Notes

Reaction equation

HRID 1295498 reaction equation
C[O:2][C:3]1(OC)[CH:8]2[CH2:9][CH2:10][CH:4]1[CH2:5][N:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:7]2>Cl>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:6]2[CH2:5][CH:4]3[C:3](=[O:2])[CH:8]([CH2:9][CH2:10]3)[CH2:7]2)=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 694287408,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane

Product 1

HCID 694284713-(4-Methoxy-benzyl)-3-aza-bicyclo[3.2.1]octan-8-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

8,8-Dimethoxy-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octane (4.88 g, 0.0167 mol) was dissolved in 1N HCl (50 mL) then heated to reflux 2 h (or until judged complete by TLC). The reaction was cooled to room temperature, washed with ether (1×50 mL), then the aqueous layer was made alkaline with 1 N NaOH and saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (4×70 mL) then CH2Cl2 (1×50 mL), washed with saturated aqueous NaCl solution (200 mL), dried over Na2SO4, filtered then concentrated to yellow oil (3.88 g, 94%). (TLC 50% EtOAc/hexanes Rf 0.55); 1H NMR (400 MHz, CDCl3) δ 7.22 (d, J=8.3 Hz, 2H), 6.83 (d, J=8.3 Hz, 2H), 3.77 (s, 3H), 3.49 (s, 2H), 2.92 (dd, J=11.4, 3.9 Hz, 2H), 2.46 (d, J=10.8 Hz, 2H), 2.12 (br s, 2H), 2.00 (dd, J=12.7, 4.6 Hz, 2H), 1.83 (m, 2H); GCMS m/z 245 (M)+.

Workup

  1. temperaturethen heated
  2. temperatureto reflux 2 h (or until judged complete by TLC)
  3. washwashed with ether (1×50 mL)
  4. extractionThe product was extracted with EtOAc (4×70 mL)
  5. washCH2Cl2 (1×50 mL), washed with saturated aqueous NaCl solution (200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthen concentrated to yellow oil (3.88 g, 94%)

Sources & evidence

ORD record
ord-4486475d038a466aa66fbbacbdb19764
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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