HCID 67995869, compound → 6-Oxa-8-azaspiro[4.5]dec-2-en-7-one, 8-[(1S)-1-(4-bromophenyl)ethyl]-

HRID 1615163Notes

Reaction equation

HRID 1615163 reaction equation
[CH2:1]([C:4]1([CH2:20]C=C)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]>ClCCl.CC1C=C(C)C=C(C)C=1N1CCN(C2C(C)=CC(C)=CC=2C)C1=C1CC(Cl)(Cl)CCC1P(=CC1C=CC=CC=1)(C1CCCCC1)C1CCCCC1.[Ru]>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C:4]3([CH2:1][CH:2]=[CH:3][CH2:20]3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 67995869HCID 67995869, compound

Product 1

HCID 565964856-Oxa-8-azaspiro[4.5]dec-2-en-7-one, 8-[(1S)-1-(4-bromophenyl)ethyl]-

Reagents, catalysts & solvents 2

HCID 131731646HCID 131731646, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)-(tricyclohexylphosphine)-ruthenium (Grubbs' 2nd generation metathesis catalyst, 1.00 g) is added to a solution of (S)-6,6-diallyl-3-[1-(4-bromo-phenyl)-ethyl]-[1,3]oxazinan-2-one (8.65 g) in dichloromethane (120 mL) at room temperature. The resulting solution is stirred at room temperature overnight and then concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:2→0:1) to afford the title compound as a greyish solid. Yield: 6.11 g (77% of theory); LC (method 1): tR=3.68 min; Mass spectrum (ESI+): m/z=336/338 (Br) [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:2→0:1)

Sources & evidence

ORD record
ord-bd485cecfd134a8c9df51659b8af1cce
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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