Diethyl Oxalate → 4-[(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]morpholine-2,3-dione

HRID 1436116Notes

Reaction equation

HRID 1436116 reaction equation
[Si:1]([O:18][C@H:19]([CH3:34])[C@H:20]([NH:30]CCO)[C:21]1[CH:26]=[C:25]([F:27])[C:24]([F:28])=[C:23]([F:29])[CH:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([O:42][CH2:43][CH3:44])(=[O:41])[C:36]([O:38]CC)=O>>[Si:1]([O:18][C@H:19]([CH3:34])[C@H:20]([N:30]1[CH2:44][CH2:43][O:42][C:35](=[O:41])[C:36]1=[O:38])[C:21]1[CH:26]=[C:25]([F:27])[C:24]([F:28])=[C:23]([F:29])[CH:22]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 689073882-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]ethanol

Product 1

HCID 689093844-[(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]morpholine-2,3-dione

Procedure

A solution of 2-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]ethanol (102 mg) in diethyl oxalate (2 ml) was stirred at 170° C. for one hour and 30 minutes. Diethyl oxalate was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate 9:1 to 6:1) to obtain 48 mg of the title compound.

Workup

  1. customDiethyl oxalate was evaporated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate 9:1 to 6:1)

Sources & evidence

ORD record
ord-ea5e28507b62453790cb70d841ccd19c
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

Loading…