Diisopropylethylamine → {2-Methyl-4-[2-(4-octylphenyl)ethyl]-4,5-dihydro-1,3-oxazol-4-yl}methanol

HRID 2304985Notes

Reaction equation

HRID 2304985 reaction equation
[NH2:1][C:2]([CH2:21][OH:22])([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)[CH2:3][OH:4].[CH2:23](C(CC)(CC)C([O-])([O-])[O-])[CH3:24].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:23][C:24]1[O:22][CH2:21][C:2]([CH2:3][OH:4])([CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=2)[N:1]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 107970FingolimodHCID 21875354Triethylorthoaceate

Product 1

HCID 71316181{2-Methyl-4-[2-(4-octylphenyl)ethyl]-4,5-dihydro-1,3-oxazol-4-yl}methanolYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 450 mg (1.5 mmol) of 2-amino-2-hydroxymethyl-4-(4-(octyl)phenyl)butanol, 0.32 mL (1.75 mmol) of triethylorthoacetate and 0.56 mL (3.2 mmol) of DIEA in 6 mL of DMF was stirred at 75° C. for 2 h. The mixture was cooled, partitioned between 40 mL of 3:1 v/v ether/EtOAc and water and the layers were separated. The organic layer was washed with water and dried. Flash chromatography on silica gel using 4:1 v/v CH2Cl2/EtOAc as the eluant afforded 440 mg (91%) of the title compound: Mass spectrum (NH3—CI) 332 (M+H).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between 40 mL of 3:1 v/v ether/EtOAc and water
  3. customthe layers were separated
  4. washThe organic layer was washed with water
  5. customdried

Sources & evidence

ORD record
ord-4b1beb8521a3490aba441ff21c678ba4
Source dataset
uspto-grants-2002_08
Patent number
US06437165B1

Reaction notes

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