Pyridine → HCID 90449619, compound

HRID 1411319Notes

Reaction equation

HRID 1411319 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16].N1C=CC=CC=1>C(Cl)Cl>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][C:15]([NH:1][CH2:2][CH:3]2[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]2)=[O:16])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 10679125Tert-butyl 3-(aminomethyl)azetidine-1-carboxylate

Product 1

HCID 90449619HCID 90449619, compoundYield 121.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(aminomethyl)azetidine-1-carboxylate (1.10 g, 5.91 mmol) was dissolved in methylene chloride (50 mL). Thereafter, 4-nitrophenyl chloroformate (1.19 g, 5.91 mmol) and pyridine (0.47 g, 5.91 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred for 16 hours. Thereafter, the reaction solution was concentrated in vacuo to obtain tert-butyl 3-((((4-nitrophenoxy)carbonyl)amino)methyl)azetidine-1-carboxylate (2.52 g, >100%) in the form of a white solid.

Workup

  1. concentrationThereafter, the reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7395ef2cdbbd4a9a948fb3a21d9436ed
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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