Hydrochloric Acid → HCID 69263087, compound

HRID 1797407Notes

Reaction equation

Br[C:2]1[C:3]([CH3:22])=[C:4]([CH3:21])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[C:6]=2[C:19]=1[CH3:20].[C:23]1([C@H:29]([NH2:31])[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:23]1([C@H:29]([NH:31][C:2]2[C:3]([CH3:22])=[C:4]([CH3:21])[C:5]3[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=4)[C:6]=3[C:19]=2[CH3:20])[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 107 °C

Procedure

Under a nitrogen atmosphere, to toluene (10 mL) were added 5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (2 g) and (R)-(+)-1-phenylethylamine (0.94 g), then palladium acetate (5 mg) and (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-dinaphthyl (41.6 mg), and further sodium tert-botoxide (0.86 g). The mixture was stirred at 107° C. for 7 hours. Diluted hydrochloric acid was added to the reaction solution. The organic layer was separated and washed with a 10% aqueous solution of sodium chloride and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which was eluted with ethyl acetate-n-hexane [1:9], to obtain the title compound (2.12 g, 95.5%).

Workup

customThe organic layer was separated
washwashed with a 10% aqueous solution of sodium chloride
concentrationconcentrated under reduced pressure
washwas eluted with ethyl acetate-n-hexane [1:9]

Sources & evidence

ORD record: ord-8295cc00c4ce4309899f563d3584546f
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034166B2

Reaction notes

Loading…