Isopropyltriphenylphosphonium iodide → 1-tert-Butoxycarbonyl-4-[N-methyl-N-(3-(2-methyl-1-propenyl)-2-pyridinyl)amino]piperidine
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[I-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:51])[C:43]2[C:48]([CH:49]=O)=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]([CH3:51])[C:43]2[C:48]([CH:49]=[C:2]([CH3:3])[CH3:1])=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]Participants
4
Procedure
Following the general procedure of EXAMPLE 16 and making non-critical variations but starting with n-butyl lithium (1.6M, 3.9 ml, 6.26 mmol), isopropyltriphenylphosphonium iodide (2.71 g, 6.26 mmol), and 1-tert-butoxycarbonyl-4-[N-methyl-N-(3-(formyl)-2-pyridinyl)amino]piperidine (XXIV, EXAMPLE 26) (1.0 g, 3.13 mmol), the title compound is obtained, NMR (300 MHz, CDCl3) 1.30, 1.50-1.59, 1.64, 1.75, 2.42-2.50, 2.61, 3.40-3.50, 3.95-4.06, 5.88, 6.62, 7.18 and 7.95δ.
Sources & evidence
- ORD record
- ord-9c07b3faec4c4f6a9ef82117e36a8bb9
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866589
Reaction notes
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