HCID 58691184, compound → benzyl [(3S,7R)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate

HRID 1392074Notes

Reaction equation

[CH3:1][N:2]([CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C=C)[C:3]([C@@H:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH:7]=[CH2:8])=[O:4]>C1(C)C=CC=CC=1.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:1][N:2]1[C@H:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:8]=[CH:7][CH2:6][C@H:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:4].[CH3:1][N:2]1[C@@H:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:8]=[CH:7][CH2:6][C@H:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]1=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of benzyl ((1S)-1-{[methyl(1-phenylprop-2-en-1-yl)amino]carbonyl}but-3-en-1-yl)carbamate (2b) (1.7 g) dissolved in Toluene (200 mL) at 80° C. under N2 was added Grubbs catalyst (2nd generation) (191 mg) and the reaction mixture was stirred at 80° C. for 1 h, cooled to RT and concentrated in vacuo. The crude product was directly purified via flash chromatography (gradient—5%, 10%, 15% and 20% EtOAc/hexanes) to give the title compound (2c) (811 mg) and benzyl [(3S,7R)-1-methyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (2d) (590 mg) (combined yield of 89%).

Workup

temperaturecooled to RT
concentrationconcentrated in vacuo
customThe crude product was directly purified via flash chromatography (gradient—5%, 10%, 15% and 20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c692fbaf60ee44bd9c31476ff18dbdb2
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342007B2

Reaction notes

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