Oxane-4-carbonyl chloride → rac-{(3R,4S)-4-(3,4-dichloro-phenyl)-1-[1-(tetrahydro-pyran-4-carbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-fluoro-phenyl ester
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:33])[N:10]([C@@H:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][N:14]([C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[O:34]1[CH2:39][CH2:38][CH:37]([C:40](Cl)=[O:41])[CH2:36][CH2:35]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:33])[N:10]([C@@H:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][N:14]([C:25]([CH:27]3[CH2:32][CH2:31][N:30]([C:40]([CH:37]4[CH2:38][CH2:39][O:34][CH2:35][CH2:36]4)=[O:41])[CH2:29][CH2:28]3)=[O:26])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1Participants
3
Reactant 2
Product 1
Procedure
In analogy to the procedure described for the synthesis of example 73, the title compound rac-{(3R,4S)-4-(3,4-dichloro-phenyl)-1-[1-(tetrahydro-pyran-4-carbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using tetrahydro-2H-pyran-4-carbonyl chloride instead of propionyl chloride and was obtained as a white foam. MS m/e: 606.3 [M]+.
Workup
- customIn analogy to the procedure described for the synthesis of example 73
- customwas obtained as a white foam
Sources & evidence
- ORD record
- ord-b8b8070f1b1c4aaaa7218a9410e7a7b5
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226916B2
Reaction notes
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