Triethyl phosphonoacetate → Ethyl (1-methylpiperidin-4-yl)acetate

HRID 586147Notes

Reaction equation

HRID 586147 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH3:9][CH2:10][O:11][C:12]([CH2:14]P(OCC)(OCC)=O)=[O:13].[H-].[Na+]>C1C=CC=CC=1>[CH2:10]([O:11][C:12](=[O:13])[CH2:14][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[CH3:9]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 740491-Methyl-4-piperidone

Product 1

HCID 11819748Ethyl (1-methylpiperidin-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(1-Methyl-piperid-4-yl)-ethanoic acid ethyl ester is prepared from 1-methyl-piperid4-one (1 equiv), triethyl phosphono acetate (1 equiv) and NaH (1.1 equiv) in benzene followed by reduction of the alkene bond according to the procedure of Cignarella etc. (J Heterocyclic Chem 1993, 30 (5), 1337-1340).

Sources & evidence

ORD record
ord-7c9ed19be62f47e9bd4ec05490ec61e9
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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