Acetic Acid → 1-Boc-4-AP

HRID 2382182Notes

Reaction equation

HRID 2382182 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[C:16]1([NH:15][CH:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 14915021-Boc-4-APYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of Boc-4-piperidone (4.0 g, 20 mmol), aniline (1.9 ml, 20 mmol), and acetic acid, glacial (1.4 ml, 24 mmol) in dichloroethane (60 mL) was added sodium triacetoxyborohydride (6.0 g, 28 mmol) portionwise at RT. The suspension was stirred at RT for 24 h, diluted with water and extracted with dichloromethane. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by ISCO using 0-30% EtOAc in Hexanes to give tert-butyl 4-(phenylamino)piperidine-1-carboxylate (2.5 g, 45% yield).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by ISCO

Sources & evidence

ORD record
ord-33d4c4dfb6de466592f7097a55af9fd7
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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