Hydrochloric Acid → N-Boc-hexahydro-1H-azepin-4-one

HRID 242537Notes

Reaction equation

HRID 242537 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.[OH-].[Na+].[C:12]([O:16][C:17](OC([O-])=O)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CC(O)(C)C.O>[C:12]([O:16][C:17]([N:5]1[CH2:6][CH2:7][CH2:8][C:2](=[O:1])[CH2:3][CH2:4]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1501891Azepan-4-oneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 1512679N-Boc-hexahydro-1H-azepin-4-oneYield 84%

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a stirred solution of 4-oxohomopiperidine.HCl (1.2 g, 8.05 mmol), NaOH (0.68 g, 16.9 mmol) in t-BuOH/H2O (1:1, 10 mL) was added t-butyldicarbonate (1.93 mL, 8.9 mmol) drop-wise. The reaction was stirred at RT overnight, extracted with EtOAc (2×10 mL) and the organic layer separated. The organic layer was dried over Na2SO4 and concentrated under vacuo. Pure 1-t-butoxycarbonyl-4-oxohomopiperidine (1.42 g, 84%) was isolated via silica gel flash chromatography eluting with 50% EtOAc/hexane.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. customthe organic layer separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-72a38cefc93941b9a6a7785939b5cf2a
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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