Nitroethane → 1,2-Dimethoxy-4-(2-nitroprop-1-enyl)benzene
Reaction equation
COC1C=C(C=CC=1OC)C[C@@H](C)N.Cl.COC1C=C(C=CC=1OC)C[C@@H](C)N.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[CH:35]=O.[N+:42]([CH2:45][CH3:46])([O-:44])=[O:43]>>[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:35]=[C:45]([N+:42]([O-:44])=[O:43])[CH3:46])[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]Participants
Procedure
A process according to Claim 1, wherein said (R)-3,4-dimethoxy-amphetamine hydrodchloride of Formula (3) is prepared by condensing 3,4-dimethoxybenzaldehyde (10) with nitroethane (Henry's reaction) to form 3,4-dimethoxy-phenyl-2-nitro-propene (11), wherein said 3,4-dimethoxy-phenyl-2-nitro-propene is then reduced to 3,4-dimethoxy-phenyl-acetone (12) by means of a catalytic hydrogenation, wherein said 3,4-dimethoxy-phenyl-acetone (12) is then reacted with (R)-α-methyl-benzyl-amine (13) to form the corresponding chiral imine (14), wherein said chiral imine (14) is then diastereoselectively reduced to (R,R)-N-phenyl-ethyl-3,4-dimethoxy-amphetamine (15) hydrochloride intermediate by means of a catalytic hydrogenation with Raney nickel with the intermediate (15) being then debenzylated by a further hydrogenation, thus yielding (R)-3,4-dimethoxy-amphetamine hydrochloride, according to the following reaction scheme: ##STR25##
Sources & evidence
- ORD record
- ord-676790c5c104454bae070857f6e0a19c
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663360
Reaction notes
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