3-Nitrophenylboronic Acid → Tert-butyl 4-(3-nitrophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 1832143Notes

Reaction equation

HRID 1832143 reaction equation
NC1C=C(C2CCN(C(OC(C)(C)C)=O)CC=2)C=CC=1.C([O-])([O-])=O.[Na+].[Na+].FC(F)(F)S(O[C:33]1[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH:38]=1)(=O)=O.[N+:48]([C:51]1[CH:52]=[C:53](B(O)O)[CH:54]=[CH:55][CH:56]=1)([O-:50])=[O:49].[Cl-].[Li+]>C(COC)OC>[N+:48]([C:51]1[CH:56]=[C:55]([C:33]2[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH:38]=2)[CH:54]=[CH:53][CH:52]=1)([O-:50])=[O:49]

Participants

7

Reactant 5

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 22049056tert-Butyl 4-(3-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 15751429Tert-butyl 4-(3-nitrophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylateYield 82.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

According to the procedure used for the synthesis of tert-butyl 4-[3-(amino)phenyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate, a mixture of 2 M aqueous Na2CO3 solution (2.2 mL), tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-1,2,3,6-tetrahydro-1-pyridine-carboxylate (0.500 g, 1.51 mmol), 3-nitrophenylboronic acid (0.353 g, 2.11 mmol), lithium chloride (0.191 g, 4.50 mmol) and tetrakistriphenylphosphine palladium (0) (0.080 g, 0.075 mmol) in dimethoxyethane (5 mL) afforded 0.380 g of the desired product.

Sources & evidence

ORD record
ord-d71e0799b4bd440e83d687a538789202
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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