Aniline → 1-Boc-4-AP

HRID 1585243Notes

Reaction equation

HRID 1585243 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 5

HCID 6115AnilineHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 14915021-Boc-4-APYield 80.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.53 g (7.68 mmol) of BOC-piperidone and 13.4 g (77 mmol) of sodium sulfate in 28 mL acetic acid were treated with 0.78 mL (8.6 mmol) of aniline. After 10 min, 8.2 g (39 mmol) of sodium triacetoxyborohydride was added. After 45 min, the solution was poured onto ice, and neutralized by portionwise addition of solid sodium bicarbonate (ca. 45 g). The resulting solution was extracted with five portions of CHCl3 ; the organics were washed with brine, dried over MgSO4, filtered, concentrated, and purified via flash chromatography (10:1 to 5:1 to 2:1 hexane-EtOAc) to provide 1.703 g of the title compound as a white solid.

Workup

  1. waitAfter 45 min
  2. additionthe solution was poured onto ice
  3. extractionThe resulting solution was extracted with five portions of CHCl3
  4. washthe organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography (10:1 to 5:1 to 2:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-f734625da8fe4bb0963771701441707d
Source dataset
uspto-grants-1999_08
Patent number
US05936089

Reaction notes

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