Methyl vinyl ketone → 3-{[(2,4-Dichlorobenzyl)-(3-oxo-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester

HRID 1435154Notes

Reaction equation

HRID 1435154 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]([C:25]([CH3:27])=[O:26])=[CH2:24]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:24][CH2:23][C:25](=[O:26])[CH3:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 690029773-[(2,4-Dichlorobenzylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 690048573-{[(2,4-Dichlorobenzyl)-(3-oxo-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-[(2,4-dichlorobenzylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester (200 mg, 0.58 mmol) in CHCl3 (3 mL) is added methyl vinyl ketone (0.12 mL, 1.45 mmol). The reaction is refluxed under N2 overnight and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 5% EtOH (10% NH4OH)/chloroform to yield 196 mg (81%) of 3-{[(2,4-dichlorobenzyl)-(3-oxo-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester. 1H NMR (400 MHz, CD3OD) δH: 7.46-7.44 (2H, m), 7.35-7.32 (1H, m), 3.95-3.91 (2H, m), 3.7 (2H, s) 3.5-3.45 (2H, m), 2.9-2.75 (3H, m), 2.74-2.65 (4H, m), 2.1 (3H, s), 1.46 (9H, s). Mass spectrum (ion spray): m/z=415.2 (M+H).

Workup

  1. temperatureThe reaction is refluxed under N2 overnight
  2. concentrationconcentrated
  3. customThe crude product is purified by flash chromatography on silica gel eluting with 5% EtOH (10% NH4OH)/chloroform

Sources & evidence

ORD record
ord-cd8d8d9869994414b3784da7200a1129
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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