(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-nitrobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one → (5R)-3-[2-(4-{2-[(3-Aminobenzyl)oxy]ethoxy}phenyl)ethyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 916800Notes

Reaction equation

HRID 916800 reaction equation
[CH3:1][C:2]1([CH3:40])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-])=O)[CH:32]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1>CCOC(C)=O.CCO.O=[Pt]=O>[NH2:37][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][O:29][CH2:28][CH2:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:14]2[CH2:13][C@@H:12]([C:10]3[CH:9]=[CH:8][C:6]4[O:7][C:2]([CH3:40])([CH3:1])[O:3][CH2:4][C:5]=4[CH:11]=3)[O:16][C:15]2=[O:17])=[CH:25][CH:24]=1

Participants

5

Reactant 1

HCID 11284238(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-nitrobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one

Product 1

HCID 11295328(5R)-3-[2-(4-{2-[(3-Aminobenzyl)oxy]ethoxy}phenyl)ethyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 86.2%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-nitrobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one (1.22 g) in EtOAc (20 mL) and EtOH (15 mL) was hydrogenated over PtO2 (122 mg) at room temperature and atmospheric pressure for 3 h. The catalyst was then removed by filtration over Celite, washed with EtOAc and concentrated in vacuo to give the title compound (994 mg). LCMS RT=3.23 min.

Workup

  1. customThe catalyst was then removed by filtration over Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd200b44f2bf492ebf9542ad53357014
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

Loading…