[3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl butyrate → [(5R)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

HRID 459016Notes

Reaction equation

HRID 459016 reaction equation
C([O:6][CH2:7][CH:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=2)[CH2:9]1)(=O)CCC>CO>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH2:9][C@H:8]([CH2:7][OH:6])[O:12][N:11]=2)=[N:14][CH:15]=1

Participants

3

Reactant 1

HCID 18442967[3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl butyrate2×

Product 1

HCID 58822457[(5R)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R,S)-[3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (prepared by hydrolysis of Intermediate 9, 3.1 g) was dissolved in hot methanol (25 ml), it was then separated by chiral column (Chiral Pak AS) eluting with 30%, isopropanol in hexanes. The title compound [(−) isomer, 1.5 g)] which eluted first from the column was collected along with the (+) isomer (second peak, 1.18 g). Chiral HPLC analysis indicated <2% of the (+) isomer was present. [α]D=−125° (c=0.0076 g/ml in methanol).

Workup

  1. customit was then separated by chiral column (Chiral Pak AS)
  2. washeluting with 30%, isopropanol in hexanes
  3. washThe title compound [(−) isomer, 1.5 g)] which eluted first from the column
  4. customwas collected along with the (+) isomer (second peak, 1.18 g)

Sources & evidence

ORD record
ord-0865e5fe702744b7be9a481379848c6c
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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