Azetidine → 6-(4,4-dimethoxycyclohexyl)-5,6-dihydropyridin-2(1H)-one

HRID 2175501Notes

Reaction equation

HRID 2175501 reaction equation
[CH3:1][O:2][C:3]1([O:18][CH3:19])[CH2:8][CH2:7][CH:6]([CH:9]([NH:13][C:14](=[O:17])[CH:15]=[CH2:16])[CH2:10]C=C)[CH2:5][CH2:4]1.N1CCC1>ClCCCl>[CH3:19][O:18][C:3]1([O:2][CH3:1])[CH2:4][CH2:5][CH:6]([CH:9]2[NH:13][C:14](=[O:17])[CH:15]=[CH:16][CH2:10]2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 68004101N-(1-(4,4-dimethoxycyclohexyl)but-3-en-1-yl)acrylamide

Product 1

HCID 680039756-(4,4-dimethoxycyclohexyl)-5,6-dihydropyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-(1-(4,4-dimethoxycyclohexyl)but-3-en-1-yl)acrylamide (512 mg, 2.4 mmol), prepared in the previous step, and the Grubbs Generation II catalyst (97 mg, 0.11 mmol) in DCE (100 mL) was degassed and heated to 50° C. under argon for 2 hours. The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (silica gel, DCM->0-5% MeOH/ethyl acetate) to afford the product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography (silica gel, DCM->0-5% MeOH/ethyl acetate)
  3. customto afford the product

Sources & evidence

ORD record
ord-dc362b343b6544f4a191078849eafa46
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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