Potassium Carbonate → (R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester

HRID 242818

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([NH2:24])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:24][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-fluoro-2-nitrobenzene (1.41 g, 10.0 mmol), (R)-3-aminopiperidine-1-carboxylic acid tertbutyl ester (2 g, 10.0 mmol) and potassium carbonate (152 mg, 11.0 mmol) in DMF (18 mL) was heated to 120° C. under microwave irradiation for 30 min. The reaction mixture was partitioned between EtOAc (150 mL) and water. The organic layer was washed with brine, dried (Na2SO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 10% EtOAc in DCM) affording (R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester as an orange oil (2.48 g, 77%). LCMS: RT 3.95 min [M+H-tBu]+ 266.2.

Workup

customThe reaction mixture was partitioned between EtOAc (150 mL) and water
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, eluant 10% EtOAc in DCM)

Sources & evidence

ORD record: ord-f0deb9b4db2e463f80f81f0487975eb6
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Linked notes

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