HCID 57519123, compound → HCID 57519124, compound

HRID 2109344Notes

Reaction equation

[CH2:1]([N:4]([CH:12]([C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40](=[O:44])[N:41]([CH3:43])[CH3:42])=[CH:35][C:34]=1C=C)[CH2:13][CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]>ClCCl.CC1C=C(C)C(N2[CH-]N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[C:29]([Si:16]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:15][CH2:14][CH2:13][CH:12]1[C:33]2[CH:34]=[CH:35][C:36]([O:39][C:40](=[O:44])[N:41]([CH3:42])[CH3:43])=[CH:37][C:38]=2[CH:3]=[CH:2][CH2:1][N:4]1[C:5]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:11])([CH3:31])([CH3:30])[CH3:32]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of t-butyl allyl-[3-(t-butyl-diphenyl-silanyloxy)-1-(4-dimethylcarbamoyloxy-2-vinyl-phenyl)-propyl]-carbamate (360 mg, 0.56 mmol) synthesized in step (j) of Example 192 in dichloromethane (40 ml) was added tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] [benzylidene] ruthenium (IV) dichloride (47.5 mg, 0.0560 mmol), and the resulting mixture was stirred for 3 hours at 45° C. under a nitrogen atmosphere. After stirring, the reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:1-2:1) as the eluent to afford the title compound (330 mg, yield: 96%) as a colorless oil

Workup

stirringAfter stirring
customthe reaction mixture was evaporated in vacuo
customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-cf2680e3414b42aea478c0a7ccb1f962
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514475B2

Reaction notes

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