Sodium borohydride → tert-butyl (3S)-4-[2-(3-cyano-4-fluorophenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10](=[O:27])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]2[CH2:25][OH:26])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[BH4-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]([OH:27])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][C@H:13]2[CH2:25][OH:26])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl (3S)-4-[2-(3-cyano-4-fluorophenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate (800 mg, 2.12 mmol) was dissolved in ethanol (50 mL) then sodium borohydride (321 mg, 8.48 mmol) was added and the mixture was stirred at RT for 16 h. LC-MS analysis showed product to be present. The ethanol was removed and the residue was redissolved in EtOAc and stirred with 1N HCl for 5 min. The mixture was then neutralized with saturated aqueous NaHCO3 and extracted twice with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to dryness to yield the title compound. LC-MS: M+1=280.
Workup
- customThe ethanol was removed
- dissolutionthe residue was redissolved in EtOAc
- stirringstirred with 1N HCl for 5 min
- extractionextracted twice with EtOAc
- washThe organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1646f88454294aa2afbce18bf7a27979
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062070B2
Reaction notes
Loading…