Water → 3-(6-Bromopyridin-3-yl)propan-1-ol

HRID 1896696Notes

Reaction equation

HRID 1896696 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([Br:13])=[CH:11][CH:12]=1)C.[BH4-].[Li+].O>C1COCC1>[Br:13][C:10]1[N:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 86251977Ethyl 3-(6-bromopyridin-3-yl)propanoate

Product 1

HCID 707008303-(6-Bromopyridin-3-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 560 mg (2.17 mmol) of 3-(6-bromopyridin-3-yl)propionic acid ethyl ester and 94.6 mg (4.34 mmol) of lithium borohydride were stirred in 40 ml of THF at 40° C. for 3 h. After cooling, the mixture was cautiously hydrolyzed with water, the precipitate was filtered off with suction, and the filtrate was concentrated and admixed with water and ethyl acetate. The organic phase was separated, washed with water and concentrated. Yield: 450 mg (96%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction
  3. concentrationthe filtrate was concentrated
  4. customThe organic phase was separated
  5. washwashed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9aeda3ff500d435aa60fa387cec9ee18
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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