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

HRID 1501981Notes

Reaction equation

HRID 1501981 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 r.t 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 desired product, which can be used for 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-69a9d84be61744a492fc7ec38df3df64
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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