Cesium carbonate → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-({4-[(diphenylmethylene)amino]benzyl}oxy)ethoxy]hexyl}-1,3-oxazolidin-2-one

HRID 1014847Notes

Reaction equation

HRID 1014847 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:53](=[NH:66])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.Br[C:68]1[CH:102]=[CH:101][C:71]([CH2:72][O:73][CH2:74][CH2:75][O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][N:83]2[CH2:87][C@@H:86]([C:88]3[CH:99]=[CH:98][C:91]4[O:92][C:93]([CH3:97])([CH3:96])[O:94][CH2:95][C:90]=4[CH:89]=3)[O:85][C:84]2=[O:100])=[CH:70][CH:69]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH3:96][C:93]1([CH3:97])[O:92][C:91]2[CH:98]=[CH:99][C:88]([C@H:86]3[O:85][C:84](=[O:100])[N:83]([CH2:82][CH2:81][CH2:80][CH2:79][CH2:78][CH2:77][O:76][CH2:75][CH2:74][O:73][CH2:72][C:71]4[CH:70]=[CH:69][C:68]([N:66]=[C:53]([C:60]5[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=5)[C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)=[CH:102][CH:101]=4)[CH2:87]3)=[CH:89][C:90]=2[CH2:95][O:94]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 66845394(5R)-3-(6-{2-[(4-bromobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 86597512(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-({4-[(diphenylmethylene)amino]benzyl}oxy)ethoxy]hexyl}-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of palladium (II) acetate (40 mg), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (166 mg) and cesium carbonate (811 mg) under nitrogen was treated with toluene (15 ml) and benzophenone imine (0.36 ml) followed by a solution of (5R)-3-(6-{2-[(4-bromobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (1.00 g) in toluene (10 ml). The stirred mixture was heated to 100° for 18 h. The mixture was cooled to 20°, dichloromethane (25 ml) was added and the mixture was filtered. The filtrate was evaporated in vacuo and the residue purified by chromatography on flash silica gel (30 mm diameter column). Elution with EtOAc-PE (3:2) gave the title compound (890 mg). LCMS RT=4.07 min.

Workup

  1. temperatureThe stirred mixture was heated to 100° for 18 h
  2. temperatureThe mixture was cooled to 20°
  3. filtrationthe mixture was filtered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue purified by chromatography on flash silica gel (30 mm diameter column)
  6. washElution with EtOAc-PE (3:2)

Sources & evidence

ORD record
ord-2d40078c127848a4b5d1648e61043501
Source dataset
uspto-grants-2011_07
Patent number
US07982067B2

Reaction notes

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