Azetidine → HCID 68003822, compound

HRID 2175504Notes

Reaction equation

HRID 2175504 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])C=C)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N1CCC1>ClCCCl>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([CH:11]3[NH:14][C:15](=[O:18])[CH:16]=[CH:17]3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 68003926N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)allyl)acrylamide

Product 1

HCID 68003822HCID 68003822, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)allyl)acrylamide (560 mg, 2.23 mmol), prepared in the previous step, and the Grubbs Generation II catalyst (95 mg, 0.11 mmol) in DCE (50 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-11c9ea52777249f891777ce2d3b07c3d
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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