Potassium Carbonate → Methyl 2-[3-(tert-butoxycarbonylamino)piperidin-1-yl]benzoate

HRID 602158Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].F[C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 130 °C

Procedure

3-(tert-Butoxycarbonylamino)piperidine (7.07 g, 35.3 mmol) was dissolved in N,N-dimethylformamide (120 mL). To this solution, potassium carbonate (9.80 g, 70.9 mmol) and methyl 2-fluorobenzoate (5.0 mL, 39.2 mmol) were added and the mixture was stirred at 130° C. for 8 hours. Subsequently, the mixture was allowed to cool, diluted with ethyl acetate, and washed sequentially with water and brine. The washed product was dried over sodium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=10:1->5:1) gave 2.34 g (20%) of the desired compound as a yellow oil.

Workup

temperatureto cool
washwashed sequentially with water and brine
dry with materialThe washed product was dried over sodium sulfate
customthe solvent was evaporated
customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=10:1->5:1)

Sources & evidence

ORD record: ord-9dc8db3ce1484354a405ca619454793f
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902367B2

Reaction notes

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