Phenol → Tert-butyl 4-{[2,6-dichloro-4-(phenylmethoxy)phenoxy]methyl}piperidinecarboxylate
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C1(O)C=CC=CC=1.[Cl:23][C:24]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[C:26]([Cl:38])[C:25]=1O>>[Cl:23][C:24]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[C:26]([Cl:38])[C:25]=1[O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1Participants
Procedure
As depicted in Scheme 1, an appropriately substituted hydroxy compound, for example, the commercially available tert-butyl 4-(hydroxymethyl)piperidinecarboxylate was coupled with a phenol (A), for example the known compound 2,6-dichloro-4-(phenylmethoxy)phenol, affording the corresponding tert-butyl 4-{[2,6-dichloro-4-(phenylmethoxy)phenoxy]methyl}piperidinecarboxylate (A1). The intermediate (A1) was in turn treated with hydrogen gas under catalytic conditions using, for example, a Parr hydrogenation apparatus, to convert the phenylmethoxy moiety of (A1) to a hydroxy moiety, thereby making the hydroxy moiety available for further reaction. The so-prepared hydroxy derivative (A2) was then reacted with an appropriate haloalkane, for example, 1,1,1,3-tetrachloropropane, under basic conditions, yielding the corresponding dihaloalkene derivative, a compound of formula I, for example, tert-butyl 4-{[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]methyl}piperidinecarboxylate. Example 1, set forth below, provides detailed methods to how compounds of formula I shown in Scheme 1 were prepared.
Sources & evidence
- ORD record
- ord-83165e965bf94ec5b2586775abc1fc45
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07671201B2
Reaction notes
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