Water → 3-(4-Bromophenyl)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazole

HRID 747216Notes

Reaction equation

HRID 747216 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 15888252[3-(4-Bromophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanol

Product 1

HCID 179544873-(4-Bromophenyl)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(5RS)-[3-(4-Bromophenyl)-4,5-dihydroisoxazol-5-yl]methanol (6.0 g, 0.023 M, see Pharmacia & Upjohn WO 98-07708), triethyl amine (3.9 mL, 0.028 M), and 4-(dimethylamino)pyridine (0.56 g, 4.58 mM), were combined in dichloromethane (36 mL). A solution of tert-butyldimethylsilyl chloride (1 M in dichloromethane, 26 mL, 0.028 M) was added and the resulting mixture was stirred at room temperature for 16 h. The resulting mixture was poured into water and extracted with dichloromethane. The combined organics were dried (magnesium sulfate), filtered and evaporated. The crude material was purified by chromatography on silica gel using 50% ethyl acetate/hexanes to give 8.4 g of the desired product.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organics were dried (magnesium sulfate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by chromatography on silica gel using 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e0bd5ebb83f84ecba8160cbead958625
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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