Benzylamine → HCID 86648684, compound

HRID 43737Notes

Reaction equation

HRID 43737 reaction equation
[CH:1]([O:4][CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)([CH3:3])[CH3:2].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:19]([NH:26][C@H:10]1[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C@H:5]1[O:4][CH:1]([CH3:3])[CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67548859HCID 67548859, compound

Product 1

HCID 86648684HCID 86648684, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of tert-butyl 3-isopropoxy-4-oxopiperidine-1-carboxylate obtained in Example (147c) (105 mg, 0.408 mmol) in 1,2-dichloroethane (2 mL) was cooled in an ice water bath. Benzylamine (87.6 μL) and sodium (triacetoxy)borohydride (212 mg, 1.0 mmol) were added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate 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) to obtain 120 mg of the title compound as a colorless oily substance (85%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0345a8b91e684a588906eb56bc06311e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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