Water → HCID 19966478, compound

HRID 977604Notes

Reaction equation

HRID 977604 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([OH:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](OC)=[O:17])[CH:11]=2)[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)(C)C.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([OH:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[CH:11]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 19966469HCID 19966469, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19966478HCID 19966478, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 180 mg of 2-bromo-6-[(2RS)-2-hydroxy-2-(3-methoxycarbonylphenyl)-ethyl]-pyridine in 4 ml of toluene is mixed under argon atmosphere at -70° C. with 0.88 ml of diisobutylaluminum hydride (20% in toluene) and stirred for 3 hours at this temperature. The reaction mixture is mixed in succession at -70° C. with 0.3 ml of isopropanol and 0.3 ml of water and stirred overnight at room temperature. The precipitate is filtered off, the filtrate is dried on sodium sulfate and concentrated by evaporation. The crude product is dissolved in 3 ml of methanol, mixed with 82 mg of sodium borohydride and stirred overnight at room temperature. The reaction mixture is acidified to pH 1 with 2 n hydrdchloric acid, shaken out with ethyl acetate, the organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-10% ethyl acetate. 103 mg of 2-bromo-6-[(2RS)-2-hydroxy-2-(3-hydroxymethylphenyl)-ethyl]-pyridine is obtained as colorless oil.

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe precipitate is filtered off
  3. customthe filtrate is dried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. dissolutionThe crude product is dissolved in 3 ml of methanol
  6. additionmixed with 82 mg of sodium borohydride
  7. stirringstirred overnight at room temperature
  8. stirringshaken out with ethyl acetate
  9. customthe organic phase is dried on sodium sulfate
  10. concentrationconcentrated by evaporation
  11. customthe residue is chromatographed on silica gel with hexane/0-10% ethyl acetate

Sources & evidence

ORD record
ord-2817acfe5ccf4feda08afb8eab466d8a
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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