1-tert-Butyl 3-methyl 3-methyl-4-oxopiperidine-1,3-dicarboxylate → HCID 66758618, compound

HRID 242584Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([CH3:19])[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1([CH3:19])[C:10]([C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)([OH:11])[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl ester 3-methyl ester (1.1 g, 4.07 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added 4-chlorophenyl magnesium bromide (12.2 mL, 12.2 mmol) dropwise over ˜½ h and then stirred at 0° C. for 1 h. The reaction was quenched with saturated solution of NH4Cl and extracted with ethyl acetate (3×). The organics were collected, dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (10% ethyl acetate/90% hexane to 20% ethyl acetate/80% hexane) to yield the title compound (1.1 g, 70%). 1H-NMR (CDCl3): δ 1.17 (s, 3H), 1.44 (s, 9H), 1.55 (m, 1H), 1.96 (d, 1H) 3.00 (m, 1H), 3.37 (m, 2H), 3.53 (s, 3H), 3.91 (m, 2H), 4.07 (d, 1H), 7.27 (d, 2H), 7.43 (d, 2H). ESI-MS m/z: 384.1 (M+1), retention time 2.95.

Workup

customThe reaction was quenched with saturated solution of NH4Cl
extractionextracted with ethyl acetate (3×)
customThe organics were collected
dry with materialdried over Mg2SO4
filtrationfiltered
customevaporated in vacuo
custompurified by Biotage flash chromatography (10% ethyl acetate/90% hexane to 20% ethyl acetate/80% hexane)

Sources & evidence

ORD record: ord-dc82fbe12f90417b8d3939e65e930558
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653096B2

Reaction notes

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