Water → 4-(5-Bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid isopropyl ester

HRID 1184686Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[CH:9]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22]2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])[CH3:10].C(OCC)(=O)C.O>CN(C)C=O>[CH:9]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]2[CH2:25][C:24]3[CH:26]=[C:27]([Br:1])[CH:28]=[CH:29][C:23]=3[O:22]2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

N-Bromo-succinimide (510 mg) is added to (4-(2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid isopropyl ester (830 mg) in N,N-dimethylformamide (20 mL). The mixture is heated to 50° C. and stirred at this temperature for 4 h. After cooling to room temperature over night, ethyl acetate and water are added and the mixture is extracted with ethyl acetate. The organic phase is washed with sodium thiosulfate solution and water and dried (Na2SO4). The solvent is evaporated and the residue is triturated with diisopropyl ether to afford the title compound as a white solid. Yield: 750 mg (71% of theory); LC (method 1): tR=1.43 min; Mass spectrum (ESI+): m/z=368 [M+H]+.

Workup

temperatureAfter cooling to room temperature over night
extractionthe mixture is extracted with ethyl acetate
washThe organic phase is washed with sodium thiosulfate solution and water
dry with materialdried (Na2SO4)
customThe solvent is evaporated
customthe residue is triturated with diisopropyl ether

Sources & evidence

ORD record: ord-2efc87c71b64487cb3d6527c4c58f6b4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669271B2

Reaction notes

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