4-Chlorobenzaldehyde → (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-ol

HRID 2250819Notes

Reaction equation

HRID 2250819 reaction equation
[NH2:1][C:2]1[C:3]([OH:22])=[C:4]([CH2:8][CH2:9][C@H:10]([OH:21])[C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Mn+3]>[Si:14]([O:13][C@@H:11]([CH3:12])[C@@H:10]([OH:21])[CH2:9][CH2:8][C:4]1[C:3]2[O:22][C:28]([C:27]3[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=3)=[N:1][C:2]=2[CH:7]=[CH:6][CH:5]=1)([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 69103771(3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol

Product 1

HCID 11775181(3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-olYield 76.3%

Reagents, catalysts & solvents 2

HCID 160554manganese(III) acetate dihydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol (P0016; 445 mg) and 4-chlorobenzaldehyde (192 mg) in toluene (15 ml) was refluxed for 2 hours. And then to the resulting mixture of the Schiffs base was added manganese triacetate (733 mg) and the reaction mixture was refluxed for 1 hour. The precipitated manganese diacetate was then separated by filtration and the solvent was removed under reduced pressure. The crude product was purified by silica gel (26 g) column chromatography eluting with hexane/ethyl acetate (20:1) to give (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-ol (P0012; 465 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. additionAnd then to the resulting mixture of the Schiffs base
  3. temperaturethe reaction mixture was refluxed for 1 hour
  4. customThe precipitated manganese diacetate was then separated by filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by silica gel (26 g) column chromatography
  7. washeluting with hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-fc95a5b2fea540de9ac4b82d826093a9
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

Loading…