Diethyl Oxalate → 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester

HRID 1711219

Reaction equation

HRID 1711219 reaction equation
C[CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11](CO)=[CH:10][C:9]=2[N+:16]([O-:18])=[O:17])[CH2:4][CH2:3]1.[CH:19]([N-]C(C)C)(C)C.[Li+].[C:27]([O:34][CH2:35][CH3:36])(=[O:33])[C:28](OCC)=[O:29]>C1COCC1.O.CCOCC>[CH2:35]([O:34][C:27](=[O:33])[C:28](=[O:29])[CH2:19][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([N:5]2[CH2:4][CH2:3][CH2:2][CH2:7][CH2:6]2)[C:9]=1[N+:16]([O-:18])=[O:17])[CH3:36]

Participants

7

Reactant 3

HCID 7268Diethyl OxalateHCID 2724682Lithium diisopropylamideHCID 28963353(4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanol

Product 1

HCID 597967713-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-methyl-2-nitro-phenyl)-piperidine (i) in THF is treated with lithium diisopropylamide (“LDA”) (1 eq), followed by diethyl oxalate (1.05 eq), at 0° C. The reaction is allowed to warm to room temperature over 90 min. The reaction is diluted with water and ether, partitioned, and the aqueous layer is washed with ether. The combined organic layers are dried over MgSO4, filtered and concentrated. Chromatography gives 3-(2-nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester (ii).

Workup

  1. custompartitioned
  2. washthe aqueous layer is washed with ether
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b64d57edf6740d3b81f185e2a7dd28d
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Linked notes

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