Water → 3-(6-Bromopyridin-3-yl)propan-1-ol
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureAfter cooling
- filtrationthe precipitate was filtered off with suction
- concentrationthe filtrate was concentrated
- customThe organic phase was separated
- washwashed with water
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9aeda3ff500d435aa60fa387cec9ee18
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518976B2
Reaction notes
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