Methanol → (S)-alpha-(2-Chloroethyl)-5-isoxazolemethanol

HRID 2179965Notes

Reaction equation

HRID 2179965 reaction equation
B.CB1[N:7]2[CH2:8][CH2:9][CH2:10][C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[Cl:23][CH2:24][CH2:25]C(C1C=CON=1)=O.[CH3:33][OH:34].[O:35]1CCCC1>>[Cl:23][CH2:24][CH2:25][C@@H:33]([C:10]1[O:35][N:7]=[CH:8][CH:9]=1)[OH:34]

Participants

6

Reactant 5

HCID 887MethanolHCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 224890493-Chloro-1-(3-isoxazolyl)-1-propanone

Product 1

HCID 55298212(S)-alpha-(2-Chloroethyl)-5-isoxazolemethanolYield 13%

Procedure

Borane (18 ml, 1M in tetrahydrofuran) was added to a solution of (3aR)-tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (1.3 ml, 1M in toluene) in tetrahydrofuran (10 ml) at −10° C. A solution of 3-chloro-1-(3-isoxazolyl)-1-propanone (Example 66(b)) (6 g, 37.6 mmol) in tetrahydrofuran (12 ml) was added slowly and then stirred at −10° C. to 20° C. for 18 h. Methanol was added and the solution was evaporated and the residue azeotroped with methanol. Purification by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (774 mg, 13%).

Workup

  1. customthe solution was evaporated
  2. customthe residue azeotroped with methanol
  3. customPurification by chromatography on silica eluting with petrol-ether

Sources & evidence

ORD record
ord-a09997bc529e4e978fcca6c31181e78c
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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