Dimethylformamide → Methyl 2(S)-(piperidin-2-on-1-yl)-3-methylbutanoate

HRID 129397Notes

Reaction equation

HRID 129397 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH:13]([CH3:15])[CH3:14])[NH:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10]Cl.[H-].[Na+].CN(C=O)C>C1COCC1>[N:5]1([C@@H:4]([CH:13]([CH3:15])[CH3:14])[C:3]([O:2][CH3:1])=[O:16])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15283803N-(5-chloropentanoyl)valine methyl ester

Product 1

HCID 15283804Methyl 2(S)-(piperidin-2-on-1-yl)-3-methylbutanoateYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 105 mg (0.42 mmol) of the product of Step A in 10 mL of dry THF was treated with 17 mg (0.43 mmol) of 60% NaH in oil dispersion at 0° C. for 1 h. TLC analysis indicated starting material was present and 2 mL of DMF was added. After 1.5 h. at 0° C., the solvent was evaporated and the mixture was worked up in the standard to give 90 mg of product.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5058ca704c5a4b7aa875c2e8aae032d9
Source dataset
uspto-grants-1995_11
Patent number
US05468733

Reaction notes

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