Sodium Carbonate → 4-[3-(4-methyl-piperidin-1-yl)4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 646895Notes

Reaction equation

HRID 646895 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([N+:21]([O-:23])=[O:22])=[C:12]([N:14]3[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]3)[CH:13]=2)OC1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH:36]=[C:35](OS(C(F)(F)F)(=O)=O)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:25]([O:29][C:30]([N:32]1[CH2:33][CH:34]=[C:35]([C:8]2[CH:9]=[CH:10][C:11]([N+:21]([O-:23])=[O:22])=[C:12]([N:14]3[CH2:15][CH2:16][CH:17]([CH3:20])[CH2:18][CH2:19]3)[CH:13]=2)[CH2:36][CH2:37]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 586384871-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-nitro-phenyl]-4-methyl-piperidine

Product 1

HCID 586385144-[3-(4-methyl-piperidin-1-yl)4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A flask is charged with 1-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-nitro-phenyl]-4-methyl-piperidine (0.090 g, 0.27 mmol) (as prepared in the previous step), 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.090 g, 0.27 mmol) (Synthesis, 993, (1991)), LiCl (0.022 g, 0.54 mmol), Pd(PPh3)4 (0.015 g, 5 mol %), 2 M Na2CO3 (0.34 mL), DME (0.80 mL) and heated at 80° C. for 30 min. The reaction was diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (2×10 mL) and brine (10 mL), and the organic layer dried over Na2SO4 and evaporated. The crude product was eluted from a 10-g SPE cartridge (silica) with 10% EtOAc/hexane to give 0.080 g (74%) of the title compound as a light yellow oil. Mass spectrum (ESI, m/z): Calcd. for C22H31N3O4, 402.2 (M+H), found 402.1.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×10 mL) and brine (10 mL)
  2. dry with materialthe organic layer dried over Na2SO4
  3. customevaporated
  4. washThe crude product was eluted from a 10-g SPE cartridge (silica) with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-97f34434fd1f44e897990c084eba974d
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

Loading…