Borane;tetrahydrofuran → HCID 178425741, compound

HRID 854326Notes

Reaction equation

HRID 854326 reaction equation
[CH3:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18]([C:20]3[NH:24][N:23]=[C:22]([C:25](O)=[O:26])[CH:21]=3)=[O:19])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.B.C1COCC1>>[OH:26][CH2:25][C:22]1[CH:21]=[C:20]([C:18]([NH:17][CH2:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]([O:7][CH2:6][C:5]3[CH:28]=[CH:29][C:2]([CH3:1])=[CH:3][CH:4]=3)=[O:9])[CH2:11][CH2:12]2)=[O:19])[NH:24][N:23]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 178425742HCID 178425742, compound

Product 1

HCID 178425741HCID 178425741, compound

Procedure

To 5-({[(1-{[(4-methylbenzyl)oxy]carbonyl}piperidin-4-yl)methyl]amino}carbonyl)-1H-pyrazole-3-carboxylic acid (50 mg, 0.13 mmol) was added BH3-THF solution (2.5 mL, 2.5 mmol, 1.0M in THE). The solution was stirred at rt for 1 h, quenched with HCl (1M) and extracted with EtOAc. The organic layer was washed with H2O dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel (gradient elution, EtOAc to 10% MeOH/EtOAc) to give 4-methylbenzyl 4-[({[3-(hydroxymethyl)-1H-pyrazol-5-yl]carbonyl}amino)methyl]piperidine-1-carboxylate.

Workup

  1. customquenched with HCl (1M)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (gradient elution, EtOAc to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-b5e5a62dbb5d47239d48b93b691edda2
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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