Borane → (R)-N-(1-Boc-piperidin-3-ylmethyl)-aniline

HRID 1246897Notes

Reaction equation

HRID 1246897 reaction equation
[C:1]1([NH:7][C:8]([C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B>C1COCC1>[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:10]([CH2:8][NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11]1)([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 6331BoraneHCID 54303026(R)-1-Boc-piperidine-3-carboxylic acid phenylamide

Product 1

HCID 20598046(R)-N-(1-Boc-piperidin-3-ylmethyl)-anilineYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-1-Boc-piperidine-3-carboxylic acid phenyl amide 26 (5.26 g, 17.28 mmol) in 20 mL of dry THF was added slowly to 34.5 mL of 1.0 M borane in THF while stirring in an ice bath. The mixture was refluxed for 2 hours, then cooled in an ice bath, and quenched with 20 mL of aqueous HCl (10%), then treated with NaOH (10%) to pH ˜10. The mixture was extracted with ethyl acetate (3×100 mL). The extracts were combined and washed with brine (2×50 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was passed through a short column (silica gel, ethyl acetate) to afford (R)—N-(1-Boc-piperidin-3-ylmethyl)-aniline 28 as a colorless oil (4.59 g, 91%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled in an ice bath
  3. customquenched with 20 mL of aqueous HCl (10%)
  4. additiontreated with NaOH (10%) to pH ˜10
  5. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  6. washwashed with brine (2×50 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter the solvent was removed

Sources & evidence

ORD record
ord-5abf888ba0124a7f8b9c5616e41b684b
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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