Sodium borohydride → HCID 66980952, compound
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:13]([C:14](OC)=[O:15])[CH2:12][N:11]([CH3:18])[C:10]2=[O:19])=[CH:5][C:4]=1[C:20]([F:23])([F:22])[F:21])#[N:2].[BH4-].[Na+]>CCO>[F:23][C:20]([F:21])([F:22])[C:4]1[CH:5]=[C:6]([N:9]2[C@@H:13]([CH2:14][OH:15])[CH2:12][N:11]([CH3:18])[C:10]2=[O:19])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (R)-methyl 3-(4-cyano-3-(trifluoromethyl)phenyl)-1-methyl-2-oxoimidazolidine-4-carboxylate (25f) (0.330 g, 1.01 mmol) in EtOH (20 mL), cooled to 0° C., Sodium borohydride (0.045 g, 1.21 mmol) was added portion wise maintaining the temperature at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for further 6 h. After completion (by TLC) the volatiles were removed under reduced pressure and the crude residue was extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to provide the crude reaction mixture which was purified by column chromatography to afford the alcohol 25g (0.21 g, 69%) as a white solid.
Workup
- temperatureThe reaction mixture was slowly warmed to room temperature
- customAfter completion (by TLC) the volatiles were removed under reduced pressure
- extractionthe crude residue was extracted with EtOAc (3×20 mL)
- dry with materialThe combined organic extracts were dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customto provide the crude
- customreaction mixture which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-89f57289508e4157a25e1c131318e192
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133182B2
Reaction notes
Loading…