Tris(furan-2-yl)phosphane → (5R)-3-{4'-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 747236Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Sn](C)(C)C)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:36][C@H:35]([CH2:37][N:38]3[CH:42]=[CH:41][N:40]=[N:39]3)[O:34][C:33]2=[O:43])=[CH:28][CH:27]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1>[Si:1]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:36][C@H:35]([CH2:37][N:38]5[CH:42]=[CH:41][N:40]=[N:39]5)[O:34][C:33]4=[O:43])=[CH:30][CH:31]=3)=[CH:17][CH:16]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-3-[4-(trimethylstannyl)phenyl]-4,5-dihydroisoxazole (0.5 g, 1.1 mmol), (5R)-3-(4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (0.49 g, 1.32 mmol), and tri-2-furylphosphine (0.051 g, 0.22 mmol) were dissolved in 1,4-dioxane (6 ml) and degassed three times. Tris (dibenzylideneacetone)palladium (0) (0.1 g, 0.11 mmol) was added and the solution was degassed three times. The solution was stirred and heated to 90° C. for 18 hours. The mixture was concentrated in vacuo and then purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent giving 0.24 g desired product.

Workup

customdegassed three times
customthe solution was degassed three times
concentrationThe mixture was concentrated in vacuo
custompurified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-e460511408834b97948fe2f9a3bfd84e
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396847B2

Reaction notes

Loading…