Methyl iodide → 3,5-Dichlorobenzyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)ethyl)piperidine-1-carboxylate

HRID 1480363Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[O:18])[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:32]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:32])[CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[O:18])[CH2:15][CH2:16]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3,5-dichlorobenzyl 4-(2-((tert-butoxycarbonyl)amino)ethyl)piperidine-1-carboxylate (step 1) (3.5 g, 8.11 mmol) in DMF (40 ml) was cooled to 0° C. 60% sodium hydride/oil (0.487 g, 12.17 mmol) was added. The solution was stirred at 0° C. for 15 mins and then was warmed to RT. Iodomethane (0.761 ml, 12.17 mmol) was added and the resulting mixture was stirred at room temperature for 5 hours. The reaction was quenched with ammonium chloride (20 ml). The mixture was diluted with water (200 ml) and extracted with EtOAc (2×200 ml). The organic portion was dried using MgSO4, filtered and concentrated under reduced pressure. The residue was applied to an 80 g silica cartridge in DCM and eluted with 0-100% EtOAc in iso-hexane to afford the title compound;

Workup

temperaturewas warmed to RT
stirringthe resulting mixture was stirred at room temperature for 5 hours
customThe reaction was quenched with ammonium chloride (20 ml)
additionThe mixture was diluted with water (200 ml)
extractionextracted with EtOAc (2×200 ml)
customThe organic portion was dried
filtrationfiltered
concentrationconcentrated under reduced pressure
washeluted with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-7b530cf3e69649fc8a9fa5142325f401
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409895B2

Reaction notes

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