Ethyl Acetate → 4-[1-(4-Cyano-3-fluorobenzyl)-5-imidazolylmethyl]-1-[3-hydroxybenzyl]-2-piperazinone

HRID 412124Notes

Reaction equation

HRID 412124 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][C:8]1=[O:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:31]([C:33]1[CH:46]=[CH:45][C:36]([CH2:37][N:38]2[C:42]([CH:43]=O)=[CH:41][N:40]=[CH:39]2)=[CH:35][C:34]=1[F:47])#[N:32].CCOC(C)=O>ClCCCl>[C:31]([C:33]1[CH:46]=[CH:45][C:36]([CH2:37][N:38]2[C:42]([CH2:43][N:10]3[CH2:11][CH2:12][N:7]([CH2:6][C:5]4[CH:14]=[CH:15][CH:16]=[C:3]([OH:2])[CH:4]=4)[C:8](=[O:13])[CH2:9]3)=[CH:41][N:40]=[CH:39]2)=[CH:35][C:34]=1[F:47])#[N:32]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 114247081-(4-Cyano-3-fluorobenzyl)-5-imidazolecarboxaldehydeHCID 185360721-[3-(Hydroxy)benzyl]-2-piperazinone hydrochloride

Product 1

HCID 185360964-[1-(4-Cyano-3-fluorobenzyl)-5-imidazolylmethyl]-1-[3-hydroxybenzyl]-2-piperazinone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the amine hydrochloride from Step K (theoretically 0.22 mmol) in 2 mL of 1,2-dichloroethane was added 4 Å powdered molecular sieves (100 mg), followed by sodium triacetoxyborohydride (70 mg, 0.33 mmol). The aldehyde from Step G (51 mg, 0.22 mmol) was added, and the reaction was stirred for 16 hours. The reaction was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a pale yellow foam.

Workup

  1. washwashed with sat. aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-404df1de74b948a895ff4ee99db0dcec
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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