4-(2-Oxiranylmethoxy)benzenecarbonitrile → 2-Hydroxy-1,1-dimethylethyl 7-[3-(4-cyanophenoxy)-2-hydroxy-propyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
Reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][N:12]([C:17]([O:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[O:18])[CH2:13]2)[CH2:9]1)C1C=CC=CC=1.[O:25]1C[CH:26]1[CH2:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1>>[C:34]([C:33]1[CH:36]=[CH:37][C:30]([O:29][CH2:28][CH:26]([OH:25])[CH2:1][N:8]2[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][N:12]([C:17]([O:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[O:18])[CH2:11]3)[CH2:15]2)=[CH:31][CH:32]=1)#[N:35]Participants
3
Procedure
2-Hydroxy-1,1-dimethylethyl 7-benzyl-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylate (from step (c) above) was debenzylated according to the method described in Example E(b) above and subsequently reacted with 4-(2-oxiranylmethoxy)benzonitrile (see Example A above) in accordance with the method described in Example 2 above to give the title compound in an overall yield of 88%.
Sources & evidence
- ORD record
- ord-cd68ff13123149c89fc0aadd13e72c17
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291475B1
Reaction notes
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