2-Pyrrolidone → HCID 53722296, compound

HRID 2403438Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22]Br)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-pyrrolidone (86 mg) in anhydrous dimethylformamide (5 ml) was added sodium hydride (45 mg). the reaction mixture was stirred under nitrogen at 50° C. for 35 minutes. 4-Bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (86 mg) in anhydrous dimethylformamide (5 ml) was added. The reaction mixture was stirred at 70° C. overnight. The solvents were removed in vacuo and the crude residue was partitioned between dichloromethane and water, the combined organic extracts were washed with brine, dried (MgSO4) and the solvents removed in vacuo to give a crude product. This was purified using flash chromatography to yield 4-(2-Oxo-pyrrolidin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester (99 mg).

Workup

stirringThe reaction mixture was stirred at 70° C. overnight
customThe solvents were removed in vacuo
customthe crude residue was partitioned between dichloromethane and water
washthe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
customthe solvents removed in vacuo
customto give a crude product
customThis was purified

Sources & evidence

ORD record: ord-5ea77c3884de4c5abd82c1c173ae1bcf
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802670B2

Reaction notes

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