3-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-acrylic acid ethyl ester → 4-(4-Ethoxycarbonyl-butyl)-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)C=CC1C=NC(C(C#N)(C)C)=C(Cl)C=1)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
The title compound was prepared analogously to step 4 of example B(29)where 4-(4-ethoxycarbonyl-but-3-enyl)-piperidine-1-carboxylic acid tert-butyl ester from step 2 above, was substituted in place of 3-[5-chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-acrylic acid ethyl ester of that example. 1H NMR (400 MHz, CDCl3): δ 0.99–1.12 (m, 2H), 1.23–1.40 (m, 8H), 1.45 (s, 9H), 1.56–1.66 (m, 4H), 2.27–2.32 (m, 2H), 2.61–2.70 (m, 2H), 4.04–4.16 (m, 4H). ESIMS (MH+): 314.
Sources & evidence
- ORD record
- ord-f31f010d211b45c09f964e10910a1a74
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07151105B2
Reaction notes
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