1-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid but-3-enyl-phenethyl-amide → 1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridin-7-one

HRID 222489

Reaction equation

HRID 222489 reaction equation
[CH2:1]([N:5]([CH2:23][CH2:24]C1C=CC=CC=1)[C:6]([CH:8]1[CH2:10][N:9]1[CH:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:12])=[O:7])[CH2:2][CH:3]=[CH2:4]>ClC1C=CC=CC=1Cl>[C:13]1([CH:11]([N:9]2[CH:8]3[C:6](=[O:7])[N:5]([CH2:23][CH2:24][C:13]4[CH:22]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:1][CH2:2][CH:3]3[CH2:4][CH2:10]2)[CH3:12])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 866010821-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid but-3-enyl-phenethyl-amide

Product 1

HCID 670032651-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridin-7-oneYield 42.7%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 3 (15 g, 58.7 mmol) in o-dichlorobenzene (100 mL) is heated at 250° C. for 1200 s in a microwave reactor. The mixture is purified by flash chromatography (silica gel; Hexane/EtOAc 1:1; second spot) to provide 5 g (33%) of the title compound as an enantiomerically pure compound. M+H+=399.32.

Workup

  1. customThe mixture is purified by flash chromatography (silica gel; Hexane/EtOAc 1:1; second spot)

Sources & evidence

ORD record
ord-4e56c7ce5e644f06852e61a808db05de
Source dataset
uspto-grants-2012_06
Patent number
US08207183B2

Linked notes

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