Trifluoroacetic acid → HCID 58780687, compound

HRID 1376025Notes

Reaction equation

HRID 1376025 reaction equation
[BH4-].[Na+].C(O)(C(F)(F)F)=O.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[C:24]#[N:25])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[CH2:24][NH2:25])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 58780610HCID 58780610, compound

Product 1

HCID 58780687HCID 58780687, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To NaBH4 (0.79 g, 20.84 mmol) in THF (20 mL) at 0° C. was added TFA (2.38 g, 20.84 mmol) dropwise. To this cooled mixture was added 4-[(2-Chloro-phenyl)-cyano-methyl)-piperazine-1-carboxylic acid tert-butyl ester (101) (1.40 g, 4.17 mmol) in THF (10 mL) dropwise. The reaction mixture was allowed to stir at room temperature for 18 h. The reaction was quenched with H2O (50 mL) and diluted with EtOAc (100 mL). The organic phase was washed with H2O (100 mL) and brine (100 mL). The crude material was purified by chromatography (silica gel 60 mesh, eluting with 10% TEA/10% MeOH in EtOAc) yielding 0.49 g (34%) pure product.

Workup

  1. customThe reaction was quenched with H2O (50 mL)
  2. additiondiluted with EtOAc (100 mL)
  3. washThe organic phase was washed with H2O (100 mL) and brine (100 mL)
  4. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 10% TEA/10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-e1a604f9058e4905bc2f390f9597d974
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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