Sodium borohydride → Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 1502083Notes

Reaction equation

HRID 1502083 reaction equation
[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([C:10](=[O:28])[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][CH:13]2[CH2:25][CH2:26][OH:27])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([CH:10]([OH:28])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14][CH:13]2[CH2:25][CH2:26][OH:27])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89619114Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 89619232Tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-oxoethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate (3.81 g, 9.40 mmol) and dissolved in EtOH (60 mL) then NaBH4 (1.42 g, 37.6 mmol) was added and the mixture was stirred for 3 h. The ethanol was evaporated and brine was added then extracted with ethyl acetate twice. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by MPLC chromatography using a 330 g ISCO Redi-sep column with 5% MeOH/DCM solvent system to yield tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate: LC-MS (IE, m/z): 408 [M+1]+;

Workup

  1. customThe ethanol was evaporated
  2. additionbrine was added
  3. extractionthen extracted with ethyl acetate twice
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by MPLC chromatography

Sources & evidence

ORD record
ord-dc1621df9171442984d96bf153286b76
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

Loading…