Potassium Carbonate → tert-butyl (3R)-4-[2-(3-cyano-4-fluorophenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 2175807Notes

Reaction equation

HRID 2175807 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:13])=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].[OH:14][CH2:15][C@@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:10]([C:9]1[CH:12]=[C:5]([C:3](=[O:4])[CH2:2][N:21]2[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:17][C@@H:16]2[CH2:15][OH:14])[CH:6]=[CH:7][C:8]=1[F:13])#[N:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 867270445-(2-Bromoacetyl)-2-fluorobenzonitrile

Product 1

HCID 86727046tert-butyl (3R)-4-[2-(3-cyano-4-fluorophenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(bromoacetyl)-2-fluorobenzonitrile (13.1 g, 0.054 mol) in DMF (160 mL) was added tert-butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate (13.1 g, 0.065 mol) and K2CO3 (11.77 g, 0.075 mol), and the mixture was stirred at RT for 3 h. The mixture was washed with water, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuum to give the title compound which was used for the next step without further purification.

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-ee10a9474f804c60ac5a5eff0392823e
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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