Benzylamine → tert-Butyl cis(+/-)-4-(benzylamino)-3-(benzyloxy)piperidine-1-carboxylate

HRID 43554Notes

Reaction equation

HRID 43554 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:23]([O:30][CH:31]1[C:36](=O)[CH2:35][CH2:34][N:33]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:32]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCCl.ClCCl>[CH2:1]([NH:8][C@H:36]1[CH2:35][CH2:34][N:33]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:32][C@H:31]1[O:30][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67506029HCID 67506029, compound

Product 1

HCID 86648570tert-Butyl cis(+/-)-4-(benzylamino)-3-(benzyloxy)piperidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Benzylamine (1.47 g, 13.7 mmol) and sodium (triacetoxy)borohydride (5.30 g, 25 mmol) were added to a solution of tert-butyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylate obtained in Example (90b) (3.81 g, 12.5 mmol) in 1,2-dichloroethane (40 mL), and the mixture was stirred at room temperature for 40 minutes. The reaction solution was diluted with dichloromethane, washed with a 1 N aqueous sodium hydroxide solution and brine, and dried over magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1) to obtain 4.34 g of the title compound as a colorless solid (91%).

Workup

  1. washwashed with a 1 N aqueous sodium hydroxide solution and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 1/1, 1/3, 0/1)

Sources & evidence

ORD record
ord-b27c85121f824b3996c596334d7236ba
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…