Homoveratrylamine → 8-[2-(3,4-Dimethoxyphenyl)ethyl]-8-azabicyclo[3.2.1]octane-3-one

HRID 727097Notes

Reaction equation

CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.[CH3:10][C:11]([CH3:13])=O.C(O)=O.C(O)=O.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH2:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C([O-])(=O)C.[Na+]>Cl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][N:32]2[CH:6]3[CH2:5][CH2:13][CH:11]2[CH2:10][C:3](=[O:4])[CH2:7]3)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

Conditions

Temperature: 10 °C

Procedure

Following a general procedure previously described (P. Doster et al. Eur. I. Med. Chem. 1984, 19, 105), 8.2 g (62 mmol) 2,5-dimethoxytetrahydrofuran were heated at 80° C. in 75 ml of 0.1N aqueous HCl for 1 h. After cooling to 10° C., 10 g (68.4 mmol) acetone dicarboxylic acid, 12.4 g (68.5 mmol) 2-(3,4-dimethoxyphenyl)ethylamine, 6.13 g (74.7 mmol) sodium acetate and 5.7 ml 12N aqueous HCl were added wile stirring. Stirring was maintained overnight at room temperature. The aqueous mixture was neutralized and extracted with methylene chloride. The organic phase was washed with brine, dried over MgSO4 and concentrated. The filtrate was concentrated and the residual oil was purified by chromatography on silica gel using ethyl acetate as eluent, affording 12 g of an oil pure by TLC.

Workup

stirringStirring
temperaturewas maintained overnight at room temperature
extractionextracted with methylene chloride
washThe organic phase was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
concentrationThe filtrate was concentrated
customthe residual oil was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-d713bbc35f4146b29d03c1cbdb9d28f5
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712284

Reaction notes

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