Sodium borohydride → N-((1-(biphenylcarbonyl)-5-hydroxypiperidin-2-yl)methyl)quinoline-8-carboxamide

HRID 60814Notes

Reaction equation

HRID 60814 reaction equation
[BH4-].[Na+].OC(C(F)(F)F)=O.[C:10]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:11]([C:16]([N:18]2[CH2:23][C:22](=[O:24])[CH2:21][CH2:20][CH:19]2[CH2:25][NH:26][C:27]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=2[N:37]=[CH:36][CH:35]=[CH:34]3)=[O:28])=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=1>CO>[C:10]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:11]([C:16]([N:18]2[CH2:23][CH:22]([OH:24])[CH2:21][CH2:20][CH:19]2[CH2:25][NH:26][C:27]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=2[N:37]=[CH:36][CH:35]=[CH:34]3)=[O:28])=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131737131HCID 131737131, compound

Product 1

HCID 77912472N-((1-(biphenylcarbonyl)-5-hydroxypiperidin-2-yl)methyl)quinoline-8-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (3.49 mmol, 0.13 g) was added to a solution of N-((1-(biphenylcarbonyl)-5-oxopiperidin-2-yl)methyl)quinoline-8-carboxamide TFA salt (0.46 mmol, 0.26 g) in MeOH (10 mL) at 0° C. in three portions. The resulting mixture was stirred at rt and the reaction was tracked by analytical HPLC. The reaction was quenched with water and extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated in vacuo to give crude residue which was purified by preparative HPLC to give desired N-((1-(biphenylcarbonyl)-5-hydroxypiperidin-2-yl)methyl)quinoline-8-carboxamide with unidentified stereochemistry (Y: 75%). MS (ESI) 466 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give crude residue which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-135b46963ec4405cbf4cdacacd62607b
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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