Tert-butyl 4-hydroxypiperidine-1-carboxylate → 1,1-dimethylethyl (3R)-3-[(6-butyl-8-quinolinyl)oxy]-1-pyrrolidinecarboxylate
Reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3C[CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].C(C1C=C2C(=C(F)C=1)N=CC=C2)CCC.C(OC(N1CC[C@@H](O)C1)=O)(C)(C)C.OC1CCN(C(OC(C)(C)C)=O)CC1>>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][C@@H:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:20]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]Participants
5
Reactant 4
Product 1
Procedure
This was prepared in an analogous manner to Intermediate 3, using 6-butyl-8-fluoroquinoline (for example, as prepared for Intermediate 2) and N-tert-butoxycarbonyl-(R)-(−)-3-pyrrolidinol (commercially available, for example, from Aldrich) instead of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate. The reaction time was 3 h instead of 1.5 h. LCMS RT=3.56 min, ES+ve m/z 371 (M+H)+.
Sources & evidence
- ORD record
- ord-89e642867d5b461e94dc57717c49772d
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884114B2
Reaction notes
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